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Roizen, Jennifer Lyn

Overview:

Inspired by small molecule natural products, the Roizen laboratories will initiate research to access improved antibiotics, and selective ion channel inhibitors, with implications for the study and treatment of cancer, heart disease, and neurological disorders. This program will begin with the development of novel reaction methods, and where appropriate these methodologies will be advanced through mechanistic investigations. New reactions will be designed to streamline access to challenging natural products, such as the guaianolide sesquiterpenes. Access to these small molecules will enable us to collaborate with colleagues to probe the biological activity of these molecular architectures.

Positions:

Assistant Professor in the Department of Chemistry

Chemistry
Trinity College of Arts & Sciences

Member of the Duke Cancer Institute

Duke Cancer Institute
School of Medicine

Education:

B.A. 2003

B.A. — Williams College

Ph.D. 2009

Ph.D. — California Institute of Technology

Grants:

Pharmacological Sciences Training Program

Administered By
Pharmacology & Cancer Biology
AwardedBy
National Institutes of Health
Role
Participating Faculty Member
Start Date
July 01, 1975
End Date
June 30, 2020

GAANN - Department of Chemistry

Administered By
Chemistry
AwardedBy
Department of Education
Role
Mentor
Start Date
September 01, 2015
End Date
August 31, 2018

MRI: Acquisition of a Triple Quadrupole LC/MS System

Administered By
Chemistry
AwardedBy
National Science Foundation
Role
Major User
Start Date
August 01, 2015
End Date
July 31, 2018

Acquisition of a MALDI-TOF Mass Spectrometer System at Duke University

Administered By
Chemistry
AwardedBy
North Carolina Biotechnology Center
Role
Major User
Start Date
March 28, 2017
End Date
March 27, 2018

Site- and Enantioselective Electrophilic Halogen-Transfer Processes

Administered By
Chemistry
AwardedBy
American Chemical Society
Role
Principal Investigator
Start Date
May 01, 2015
End Date
August 31, 2017
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Publications:

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

A novel Suzuki-Miyaura protocol is described that enables the exhaustive alkylation of polychlorinated pyridines. This method facilitates a formal synthesis of normuscopyridine and the rapid assembly of a dumbbell shaped portion of a [2]rotaxane.

Authors
Laulhé, S; Blackburn, JM; Roizen, JL
MLA Citation
Laulhé, S, Blackburn, JM, and Roizen, JL. "Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters." Chemical communications (Cambridge, England) (March 27, 2017).
PMID
28345090
Source
epmc
Published In
Chemical Communications
Publish Date
2017
DOI
10.1039/c7cc00997f

Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade.

An enantioselective and diastereoselective approach toward the synthesis of the polycyclic norditerpenoid ineleganolide is disclosed. A palladium-catalyzed enantioselective allylic alkylation is employed to stereoselectively construct the requisite chiral tertiary ether and facilitate the synthesis of a 1,3-cis-cyclopentenediol building block. Careful substrate design enabled the convergent assembly of the ineleganolide [6,7,5,5]-tetracyclic scaffold by a diastereoselective cyclopropanation-Cope rearrangement cascade under unusually mild conditions. Computational evaluation of ground state energies of late-stage synthetic intermediates was used to guide synthetic development and aid in the investigation of the conformational rigidity of these highly constrained and compact polycyclic structures. This work represents the first successful synthesis of the core structure of any member of the polycyclic norcembranoid diterpene family of natural products. Advanced synthetic manipulations generated a series of natural product-like compounds that were shown to possess selective secretory antagonism of either interleukin-5 or interleukin-17. This bioactivity stands in contrast to the known antileukemic activity of ineleganolide and suggests the norcembranoid natural product core may serve as a useful scaffold for the development of diverse therapeutics.

Authors
Craig, RA; Roizen, JL; Smith, RC; Jones, AC; Virgil, SC; Stoltz, BM
MLA Citation
Craig, RA, Roizen, JL, Smith, RC, Jones, AC, Virgil, SC, and Stoltz, BM. "Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade." Chemical science 8.1 (January 2017): 507-514.
PMID
28239443
Source
epmc
Published In
Chemical Science
Volume
8
Issue
1
Publish Date
2017
Start Page
507
End Page
514
DOI
10.1039/c6sc03347d

Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Herein, we describe two novel Suzuki-Miyaura protocols that enable selective conversion of polychlorinated aromatics, with a focus on reactions to convert 2,6-dichloropyridines to 2-chloro-6-alkylpyridines or 2-aryl-6-alkylpyridines.

Authors
Laulhé, S; Blackburn, JM; Roizen, JL
MLA Citation
Laulhé, S, Blackburn, JM, and Roizen, JL. "Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters." Organic letters 18.17 (September 2016): 4440-4443.
PMID
27537216
Source
epmc
Published In
Organic Letters
Volume
18
Issue
17
Publish Date
2016
Start Page
4440
End Page
4443
DOI
10.1021/acs.orglett.6b02323

Analyzing site selectivity in Rh2(esp)2-catalyzed intermolecular C-H amination reactions.

Predicting site selectivity in C-H bond oxidation reactions involving heteroatom transfer is challenged by the small energetic differences between disparate bond types and the subtle interplay of steric and electronic effects that influence reactivity. Herein, the factors governing selective Rh2(esp)2-catalyzed C-H amination of isoamylbenzene derivatives are investigated, where modification to both the nitrogen source, a sulfamate ester, and substrate are shown to impact isomeric product ratios. Linear regression mathematical modeling is used to define a relationship that equates both IR stretching parameters and Hammett σ(+) values to the differential free energy of benzylic versus tertiary C-H amination. This model has informed the development of a novel sulfamate ester, which affords the highest benzylic-to-tertiary site selectivity (9.5:1) observed for this system.

Authors
Bess, EN; DeLuca, RJ; Tindall, DJ; Oderinde, MS; Roizen, JL; Du Bois, J; Sigman, MS
MLA Citation
Bess, EN, DeLuca, RJ, Tindall, DJ, Oderinde, MS, Roizen, JL, Du Bois, J, and Sigman, MS. "Analyzing site selectivity in Rh2(esp)2-catalyzed intermolecular C-H amination reactions." Journal of the American Chemical Society 136.15 (April 8, 2014): 5783-5789.
Website
http://hdl.handle.net/10161/13797
PMID
24673332
Source
epmc
Published In
Journal of the American Chemical Society
Volume
136
Issue
15
Publish Date
2014
Start Page
5783
End Page
5789
DOI
10.1021/ja5015508

ChemInform Abstract: Selective Intermolecular Amination of C-H Bonds at Tertiary Carbon Centers.

Authors
Roizen, JL; Zalatan, DN; Du Bois, J
MLA Citation
Roizen, JL, Zalatan, DN, and Du Bois, J. "ChemInform Abstract: Selective Intermolecular Amination of C-H Bonds at Tertiary Carbon Centers." ChemInform 45.13 (April 1, 2014): no-no.
Source
crossref
Published In
ChemInform
Volume
45
Issue
13
Publish Date
2014
Start Page
no
End Page
no
DOI
10.1002/chin.201413051

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation.

Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of "classic" natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

Authors
Liu, Y; Liniger, M; McFadden, RM; Roizen, JL; Malette, J; Reeves, CM; Behenna, DC; Seto, M; Kim, J; Mohr, JT; Virgil, SC; Stoltz, BM
MLA Citation
Liu, Y, Liniger, M, McFadden, RM, Roizen, JL, Malette, J, Reeves, CM, Behenna, DC, Seto, M, Kim, J, Mohr, JT, Virgil, SC, and Stoltz, BM. "Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation." Beilstein journal of organic chemistry 10 (January 2014): 2501-2512.
PMID
25383121
Source
epmc
Published In
Beilstein journal of organic chemistry
Volume
10
Publish Date
2014
Start Page
2501
End Page
2512
DOI
10.3762/bjoc.10.261

Speciation and decomposition pathways of ruthenium catalysts used for selective C–H hydroxylation

Authors
Flender, C; Adams, AM; Roizen, JL; McNeill, E; Du Bois, J; Zare, RN
MLA Citation
Flender, C, Adams, AM, Roizen, JL, McNeill, E, Du Bois, J, and Zare, RN. "Speciation and decomposition pathways of ruthenium catalysts used for selective C–H hydroxylation." Chemical Science 5.8 (2014): 3309-3309.
Source
crossref
Published In
Chemical Science
Volume
5
Issue
8
Publish Date
2014
Start Page
3309
End Page
3309
DOI
10.1039/c4sc01050g

Selective Intermolecular Amination of CH Bonds at Tertiary Carbon Centers

Authors
Roizen, JL; Zalatan, DN; Du Bois, J
MLA Citation
Roizen, JL, Zalatan, DN, and Du Bois, J. "Selective Intermolecular Amination of CH Bonds at Tertiary Carbon Centers." Angewandte Chemie 125.43 (October 18, 2013): 11553-11556.
Source
crossref
Published In
Angewandte Chemie International Edition
Volume
125
Issue
43
Publish Date
2013
Start Page
11553
End Page
11556
DOI
10.1002/ange.201304238

Selective intermolecular amination of C-H bonds at tertiary carbon centers.

C-H insertion: A method for intermolecular amination of tertiary CH bonds is described that uses limiting amounts of substrate and a convenient phenol-derived nitrogen source. Structure-selectivity and mechanistic studies suggest that steric interaction between the substrate and active oxidant is the principal determinant of product selectivity.

Authors
Roizen, JL; Zalatan, DN; Du Bois, J
MLA Citation
Roizen, JL, Zalatan, DN, and Du Bois, J. "Selective intermolecular amination of C-H bonds at tertiary carbon centers." Angew Chem Int Ed Engl 52.43 (October 18, 2013): 11343-11346.
PMID
24000186
Source
pubmed
Published In
Angewandte Chemie International Edition
Volume
52
Issue
43
Publish Date
2013
Start Page
11343
End Page
11346
DOI
10.1002/anie.201304238

Bridging the gap between research and teaching: A C-H insertion project

Authors
Cox, CT; Nam, S; Koenig, J; Ortega, C; Roizen, JL; Du Bois, J
MLA Citation
Cox, CT, Nam, S, Koenig, J, Ortega, C, Roizen, JL, and Du Bois, J. "Bridging the gap between research and teaching: A C-H insertion project." September 8, 2013.
Source
wos-lite
Published In
ACS National Meeting Book of Abstracts
Volume
246
Publish Date
2013

Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.

A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.

Authors
Craig, RA; Roizen, JL; Smith, RC; Jones, AC; Stoltz, BM
MLA Citation
Craig, RA, Roizen, JL, Smith, RC, Jones, AC, and Stoltz, BM. "Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block." Org Lett 14.22 (November 16, 2012): 5716-5719.
PMID
23101616
Source
pubmed
Published In
Organic Letters
Volume
14
Issue
22
Publish Date
2012
Start Page
5716
End Page
5719
DOI
10.1021/ol3027297

Capturing fleeting intermediates in a catalytic C-H amination reaction cycle.

We have applied an ambient ionization technique, desorption electrospray ionization MS, to identify transient reactive species of an archetypal C-H amination reaction catalyzed by a dirhodium tetracarboxylate complex. Using this analytical method, we have detected previously proposed short-lived reaction intermediates, including two nitrenoid complexes that differ in oxidation state. Our findings suggest that an Rh-nitrene oxidant can react with hydrocarbon substrates through a hydrogen atom abstraction pathway and raise the intriguing possibility that two catalytic C-H amination pathways may be operative in a typical bulk solution reaction. As highlighted by these results, desorption electrospray ionization MS should have broad applicability for the mechanistic study of catalytic processes.

Authors
Perry, RH; Cahill, TJ; Roizen, JL; Du Bois, J; Zare, RN
MLA Citation
Perry, RH, Cahill, TJ, Roizen, JL, Du Bois, J, and Zare, RN. "Capturing fleeting intermediates in a catalytic C-H amination reaction cycle." Proc Natl Acad Sci U S A 109.45 (November 6, 2012): 18295-18299.
PMID
23091019
Source
pubmed
Published In
Proceedings of the National Academy of Sciences of USA
Volume
109
Issue
45
Publish Date
2012
Start Page
18295
End Page
18299
DOI
10.1073/pnas.1207600109

Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

For more than a century, chemists have endeavored to discover and develop reaction processes that enable the selective oxidation of hydrocarbons. In the 1970s, Abramovitch and Yamada described the synthesis and electrophilic reactivity of sulfonyliminoiodinanes (RSO(2)N═IPh), demonstrating the utility of this new class of reagents to function as nitrene equivalents. Subsequent investigations by Breslow, Mansuy, and Müller would show such oxidants to be competent for alkene and saturated hydrocarbon functionalization when combined with transition metal salts or metal complexes, namely those of Mn, Fe, and Rh. Here, we trace our own studies to develop N-atom transfer technologies for C-H and π-bond oxidation. This Account discusses advances in both intra- and intermolecular amination processes mediated by dirhodium and diruthenium complexes, as well as the mechanistic foundations of catalyst reactivity and arrest. Explicit reference is given to questions that remain unanswered and to problem areas that are rich for discovery. A fundamental advance in amination technology has been the recognition that iminoiodinane oxidants can be generated in situ in the presence of a metal catalyst that elicits subsequent N-atom transfer. Under these conditions, both dirhodium and diruthenium lantern complexes function as competent catalysts for C-H bond oxidation with a range of nitrogen sources (e.g., carbamates, sulfamates, sulfamides, etc.), many of which will not form isolable iminoiodinane equivalents. Practical synthetic methods and applications thereof have evolved in parallel with inquiries into the operative reaction mechanism(s). For the intramolecular dirhodium-catalyzed process, the body of experimental and computational data is consistent with a concerted asynchronous C-H insertion pathway, analogous to the consensus mechanism for Rh-carbene transfer. Other studies reveal that the bridging tetracarboxylate ligand groups, which shroud the dirhodium core, are labile to exchange under standard reaction conditions. This information has led to the generation of chelating dicarboxylate dinuclear rhodium complexes, exemplified by Rh(2)(esp)(2). The performance of this catalyst system is unmatched by other dirhodium complexes in both intra- and intermolecular C-H amination reactions. Tetra-bridged, mixed-valent diruthenium complexes function as effective promoters of sulfamate ester oxidative cyclization. These catalysts can be crafted with ligand sets other than carboxylates and are more resistant to oxidation than their dirhodium counterparts. A range of experimental and computational mechanistic data amassed with the tetra-2-oxypyridinate diruthenium chloride complex, [Ru(2)(hp)(4)Cl], has established the insertion event as a stepwise pathway involving a discrete radical intermediate. These data contrast dirhodium-catalyzed C-H amination and offer a cogent model for understanding the divergent chemoselectivity trends observed between the two catalyst types. This work constitutes an important step toward the ultimate goal of achieving predictable, reagent-level control over product selectivity.

Authors
Roizen, JL; Harvey, ME; Du Bois, J
MLA Citation
Roizen, JL, Harvey, ME, and Du Bois, J. "Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds." Acc Chem Res 45.6 (June 19, 2012): 911-922.
PMID
22546004
Source
pubmed
Published In
Accounts of Chemical Research
Volume
45
Issue
6
Publish Date
2012
Start Page
911
End Page
922
DOI
10.1021/ar200318q

Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

α-Quaternary ketones are accessed through novel enantioselective alkylations of allyl and propargyl electrophiles by unstabilized prochiral enolate nucleophiles in the presence of palladium complexes with various phosphinooxazoline (PHOX) ligands. Excellent yields and high enantiomeric excesses are obtained from three classes of enolate precursor: enol carbonates, enol silanes, and racemic β-ketoesters. Each of these substrate classes functions with nearly identical efficiency in terms of yield and enantioselectivity. Catalyst discovery and development, the optimization of reaction conditions, the exploration of reaction scope, and applications in target-directed synthesis are reported. Experimental observations suggest that these alkylation reactions occur through an unusual inner-sphere mechanism involving binding of the prochiral enolate nucleophile directly to the palladium center.

Authors
Behenna, DC; Mohr, JT; Sherden, NH; Marinescu, SC; Harned, AM; Tani, K; Seto, M; Ma, S; Novák, Z; Krout, MR; McFadden, RM; Roizen, JL; Enquist, JA; White, DE; Levine, SR; Petrova, KV; Iwashita, A; Virgil, SC; Stoltz, BM
MLA Citation
Behenna, DC, Mohr, JT, Sherden, NH, Marinescu, SC, Harned, AM, Tani, K, Seto, M, Ma, S, Novák, Z, Krout, MR, McFadden, RM, Roizen, JL, Enquist, JA, White, DE, Levine, SR, Petrova, KV, Iwashita, A, Virgil, SC, and Stoltz, BM. "Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies." Chemistry 17.50 (December 9, 2011): 14199-14223.
PMID
22083969
Source
pubmed
Published In
Chemistry - A European Journal
Volume
17
Issue
50
Publish Date
2011
Start Page
14199
End Page
14223
DOI
10.1002/chem.201003383

ChemInform Abstract: Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters.

Authors
Seto, M; Roizen, JL; Stoltz, BM
MLA Citation
Seto, M, Roizen, JL, and Stoltz, BM. "ChemInform Abstract: Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters." ChemInform 39.52 (December 23, 2008).
Source
crossref
Published In
ChemInform
Volume
39
Issue
52
Publish Date
2008
DOI
10.1002/chin.200852162

Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters

Authors
Seto, M; Roizen, JL; Stoltz, BM
MLA Citation
Seto, M, Roizen, JL, and Stoltz, BM. "Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters." Angewandte Chemie 120.36 (August 25, 2008): 6979-6982.
Source
crossref
Published In
Angewandte Chemie International Edition
Volume
120
Issue
36
Publish Date
2008
Start Page
6979
End Page
6982
DOI
10.1002/ange.200801424

ChemInform Abstract: Total Synthesis of (-)-Hennoxazole A (I).

Authors
Smith, TE; Kuo, W-H; Balskus, EP; Bock, VD; Roizen, JL; Theberge, AB; Carroll, KA; Kurihara, T; Wessler, JD
MLA Citation
Smith, TE, Kuo, W-H, Balskus, EP, Bock, VD, Roizen, JL, Theberge, AB, Carroll, KA, Kurihara, T, and Wessler, JD. "ChemInform Abstract: Total Synthesis of (-)-Hennoxazole A (I)." ChemInform 39.20 (May 13, 2008).
Source
crossref
Published In
ChemInform
Volume
39
Issue
20
Publish Date
2008
DOI
10.1002/chin.200820213

Total synthesis of (-)-hennoxazole A.

An enantioselective, convergent total synthesis of the antiviral marine natural product (-)-hennoxazole A is completed in 14 steps (longest linear sequence) from commercially available 4-methyloxazole-2-carboxylic acid. Synthesis of the C(1)-C(15) pyran/bisoxazole fragment takes advantage of an aldol-like coupling between a dimethyl acetal and an N-acetylthiazolidinethione for the direct, stereoselective installation of the C(8)-methoxy-bearing stereocenter. A one-pot acetoacetate acylation/decarboxylation/cyclodehydration of another elaborate thiazolidinethione allows for rapid assembly of the pyran-based ring system. Synthesis of the C(15)-C(25) skipped triene side chain fragment makes use of a [2,3]-Wittig-Still rearrangement for efficient installation of the trisubstituted Z-double bond. Key late-stage coupling of the two fragments is effected by deprotonation of the methyl group on the bisoxazole system using lithium diethylamide, followed by alkylation with an allylic bromide side chain segment to form the C(15)-C(16) bond.

Authors
Smith, TE; Kuo, W-H; Balskus, EP; Bock, VD; Roizen, JL; Theberge, AB; Carroll, KA; Kurihara, T; Wessler, JD
MLA Citation
Smith, TE, Kuo, W-H, Balskus, EP, Bock, VD, Roizen, JL, Theberge, AB, Carroll, KA, Kurihara, T, and Wessler, JD. "Total synthesis of (-)-hennoxazole A." J Org Chem 73.1 (January 4, 2008): 142-150.
PMID
18052386
Source
pubmed
Published In
The Journal of Organic Chemistry
Volume
73
Issue
1
Publish Date
2008
Start Page
142
End Page
150
DOI
10.1021/jo7018015

Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to Calpha-tetrasubstituted hydroxyketones, acids, and esters.

Authors
Seto, M; Roizen, JL; Stoltz, BM
MLA Citation
Seto, M, Roizen, JL, and Stoltz, BM. "Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to Calpha-tetrasubstituted hydroxyketones, acids, and esters." Angew Chem Int Ed Engl 47.36 (2008): 6873-6876.
PMID
18651681
Source
pubmed
Published In
Angewandte Chemie International Edition
Volume
47
Issue
36
Publish Date
2008
Start Page
6873
End Page
6876
DOI
10.1002/anie.200801424

Total Synthesis of (-)-Hennoxazole A.

Authors
Smith, TE; Kuo, W-H; Bock, VD; Roizen, JL; Balskus, EP; Theberge, AB
MLA Citation
Smith, TE, Kuo, W-H, Bock, VD, Roizen, JL, Balskus, EP, and Theberge, AB. "Total Synthesis of (-)-Hennoxazole A." ChemInform 38.31 (July 31, 2007).
Source
crossref
Published In
ChemInform
Volume
38
Issue
31
Publish Date
2007
DOI
10.1002/chin.200731170

Total synthesis of (-)-hennoxazole A.

An enantioselective, convergent, total synthesis of the antiviral marine natural product (-)-hennoxazole A has been completed in 17 steps, longest linear sequence, from serine methyl ester and in 9 steps from an achiral bisoxazole intermediate. Elaboration of a thiazolidinethione allowed for rapid assembly of the pyran-based ring system. Key late-stage coupling was effected by deprotonation of the bisoxazole methyl group, followed by alkylation with an allylic bromide side chain segment. [structure: see text]

Authors
Smith, TE; Kuo, W-H; Bock, VD; Roizen, JL; Balskus, EP; Theberge, AB
MLA Citation
Smith, TE, Kuo, W-H, Bock, VD, Roizen, JL, Balskus, EP, and Theberge, AB. "Total synthesis of (-)-hennoxazole A." Org Lett 9.6 (March 15, 2007): 1153-1155.
PMID
17316014
Source
pubmed
Published In
Organic Letters
Volume
9
Issue
6
Publish Date
2007
Start Page
1153
End Page
1155
DOI
10.1021/ol070244p
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