Expedient Approach to ,-Unsaturated -Lactones through a Catalytic Asymmetric [2+2] Cycloaddition

被引：2

作者：

Rousseau, Anais ^{[1
]}

Buchotte, Marie ^{[1
]}

Guillot, Regis ^{[1
]}

Vincent, Guillaume ^{[1
,2
]}

Kouklovsky, Cyrille ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France

[2] Univ Paris Saclay, Univ Paris Sud, CNRS, F-91405 Orsay, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 45期

关键词：

Cycloaddition; Asymmetric catalysis; Lactones; Ketenes; Aldehydes; ANTIFUNGAL ANTIBIOTICS PHOSLACTOMYCINS; HALIDE-ALDEHYDE CYCLOCONDENSATIONS; COLONY-STIMULATING FACTORS; FAMILY INDUCE PRODUCTION; MARROW STROMAL CELLS; LEUSTRODUCSIN-B; ALPHA; BETA-UNSATURATED LACTONES; MICROBIAL METABOLITES; NATURAL-PRODUCTS; STREPTOMYCES SP;

D O I：

10.1002/ejoc.201701336

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of the cis-,-disubstituted ,-unsaturated -lactone fragment of the leustroducsins or phoslactomycins was accomplished. The new synthetic strategy involves a catalytic asymmetric ketene-aldehyde [2+2] cycloaddition leading to the formation of a cis-disubstituted -lactone. Ring extension by enolate condensation and subsequent recyclisation then gave the target -lactone in a straightforward fashion. Coupling studies with cyclohexanone are also reported.

引用

页码：6804 / 6810

页数：7

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