Stereoselective synthesis of polyketide fragments using a novel intramolecular Claisen-like condensation/reduction sequence

被引：29

作者：

Hinterding, K ^{[1
]}

Singhanat, S ^{[1
]}

Oberer, L ^{[1
]}

机构：

[1] Novartis Pharma AG, Transplantat Res, CH-4002 Basel, Switzerland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(01)01840-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Claisen-type cleavage of the Evans-oxazolidinone with an acetate enolate followed by reduction of the resulting ketone using a borane-amine complex yielded beta -hydroxy-delta -lactones as fully functionalized polyketide precursors stereoselectively. Consequently, this reaction sequence constitutes a highly practical alternative to an acetate-aldol reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8463 / 8465

页数：3

共 14 条

[1]

[Anonymous], [No title captured]

[2] SYNTHESIS OF CONFORMATIONALLY RESTRICTED RELATIVES OF THE MEVINIC ACIDS [J].

BENNETT, F ;

FENTON, G ;

KNIGHT, DW .

TETRAHEDRON, 1994, 50 (17) :5147-5158

[3] INTRAMOLECULAR CLAISEN-TYPE CONDENSATIONS OF BETA-ACETOXY AMIDES OR IMIDES [J].

BRANDANGE, S ;

LEIJONMARCK, H .

TETRAHEDRON LETTERS, 1992, 33 (21) :3025-3028

[4]

BRANDANGE S, 1983, J CHEM SOC CHEM COMM, P1097

[5]

Braun M, 1995, METHODS ORGANIC CH E, VE 21b, P1603

[6] POLYETHER IONOPHORES [J].

DUTTON, CJ ;

BANKS, BJ ;

COOPER, CB .

NATURAL PRODUCT REPORTS, 1995, 12 (02) :165-181

[7] Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp A92-308110 -: II.: Structure elucidation, stereochemistry and physico-chemical properties [J].

Fehr, T ;

Kallen, J ;

Oberer, L ;

Sanglier, JJ ;

Schilling, W .

JOURNAL OF ANTIBIOTICS, 1999, 52 (05) :474-479

[8]

GAGE JR, 1989, ORG SYNTH, V68, P77

[9] BIOSYNTHESIS OF FATTY-ACID AND POLYKETIDE METABOLITES [J].

OHAGAN, D .

NATURAL PRODUCT REPORTS, 1995, 12 (01) :1-32

[10]

RAIMUNDO BC, 1995, SYNLETT, P1213

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