A flexible route to (5R)-thiolactomycin, a naturally occurring inhibitor of fatty acid synthesis

被引：50

作者：

McFadden, JM ^{[1
]}

Frehywot, GL ^{[1
]}

Townsend, CA ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 22期

关键词：

D O I：

10.1021/ol026685k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graphic A new and efficient asymmetric synthesis of naturally occurring (5R)-thiolactomycin (1) using D-alanine as the source of chirality is described.

引用

页码：3859 / 3862

页数：4

共 31 条

[1] THERMAL RACEMIZATION OF ALLYLIC SULFOXIDES AND INTERCONVERSION OF ALLYLIC SULFOXIDES AND SULFENATES - MECHANISM AND STEREOCHEMISTRY [J].

BICKART, P ;

CARSON, FW ;

JACOBUS, J ;

MILLER, EG ;

MISLOW, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (18) :4869-&

[2] Bacterial fatty acid biosynthesis: Targets for antibacterial drug discovery [J].

Campbell, JW ;

Cronan, JE .

ANNUAL REVIEW OF MICROBIOLOGY, 2001, 55 :305-332

[3] AN ASYMMETRIC-SYNTHESIS OF THIOTETRONIC ACIDS USING CHIRALITY TRANSFER VIA AN ALLYL XANTHATE-TO-DITHIOCARBONATE REARRANGEMENT - X-RAY CRYSTAL-STRUCTURE OF (5R)-2,5-DIHYDRO-4-HYDROXY-5-METHYL-3-PHENYL-5-PROP-1'-ENYL-2-OXOTHIOPHENE [J].

CHAMBERS, MS ;

THOMAS, EJ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (16) :1228-1230

[4] Asymmetric synthesis of 5,5-disubstituted thiotetronic acids using allyl xanthate to dithiocarbonate rearrangement: Total synthesis of (5S)-thiolactomycin with revision of the absolute configuration of the natural product [J].

Chambers, MS ;

Thomas, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04) :417-431

[5] TOTAL SYNTHESIS OF (5S)-THIOLACTOMYCIN - REVISION OF THE ABSOLUTE-CONFIGURATION OF THE NATURAL PRODUCT [J].

CHAMBERS, MS ;

THOMAS, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (01) :23-24

[6] INFLUENCE OF OPTICALLY ACTIVE ACYL GROUPS ON THE ENZYMATIC HYDROLYSIS OF N-ACYLATED-L-AMINO ACIDS [J].

FU, SCJ ;

BIRNBAUM, SM ;

GREENSTEIN, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (23) :6054-6058

[7] Lipid biosynthesis as a target for antibacterial agents [J].

Heath, RJ ;

White, SW ;

Rock, CO .

PROGRESS IN LIPID RESEARCH, 2001, 40 (06) :467-497

[8] Novel inhibitors of the condensing enzymes of the Type II fatty acid synthase of pea (Pisum sativum) [J].

Jones, AL ;

Herbert, D ;

Rutter, AJ ;

Dancer, JE ;

Harwood, JL .

BIOCHEMICAL JOURNAL, 2000, 347 (pt 1) :205-209

[9] Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis [J].

Kremer, L ;

Douglas, JD ;

Baulard, AR ;

Morehouse, C ;

Guy, MR ;

Alland, D ;

Dover, LG ;

Lakey, JH ;

Jacobs, WR ;

Brennan, PJ ;

Minnikin, DE ;

Besra, GS .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (22) :16857-16864

[10] Synthesis and antitumor activity of an inhibitor of fatty acid synthase [J].

Kuhajda, FP ;

Pizer, ES ;

Li, JN ;

Mani, NS ;

Frehywot, GL ;

Townsend, CA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (07) :3450-3454

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