Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative

被引：17

作者：

Ohata, K

Terashima, S

机构：

[1] Kyorin Pharmaceut Co Ltd, Discovery Res Labs, Shimotsuga, Tochigi 3290114, Japan

[2] Sagami Chem Res Ctr, Ayase, Kanagawa 2521193, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 16期

关键词：

antibiotic; inhibitor of fatty acid synthase; deconjugative asymmetric alpha-sulfenylation;

D O I：

10.1016/j.tetlet.2006.02.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting with commercially available tiglic aldehyde, the title synthesis was achieved by employing deconjugative asymmetric alpha-sulfenylation of the chiral 3-(alpha,beta,gamma,delta-unsaturated acyl)-2-oxazolidinone with a methanethiosulfonate as a key step. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2787 / 2791

页数：5

相关论文

共 23 条

[1]

CHAMBERS CL, 1987, J CHEM SOC CHEM COMM, P1228

[2] 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

[3] 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

[4] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[5]

Fujiki K, 2002, SYNTHESIS-STUTTGART, P343

[6] MECHANISM OF ACTION OF THE ANTIBIOTIC THIOLACTOMYCIN INHIBITION OF FATTY-ACID SYNTHESIS OF ESCHERICHIA-COLI [J].

HAYASHI, T ;

YAMAMOTO, O ;

SASAKI, H ;

KAWAGUCHI, A ;

OKAZAKI, H .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1983, 115 (03) :1108-1113

[7] LITHIUM-INITIATED IMIDE FORMATION - A SIMPLE METHOD FOR N-ACYLATION OF 2-OXAZOLIDINONES AND BORNANE-2,10-SULTAM [J].

HO, GJ ;

MATHRE, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2271-2273

[8] Novel stereoselective construction of a quaternary carbon: application to synthesis of the cyclopentenedione moiety of madindolines [J].

Hosokawa, S ;

Sekiguchi, K ;

Enemoto, M ;

Kobayashi, S .

TETRAHEDRON LETTERS, 2000, 41 (33) :6429-6433

[9]

JACKOWSKI S, 1989, J BIOL CHEM, V264, P7624

[10] Analogues of thiolactomycin as potential anti-malarial and anti-trypanosomal agents [J].

Jones, SM ;

Urch, JE ;

Brun, R ;

Harwood, JL ;

Berry, C ;

Gilbert, IH .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (04) :683-692