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
收藏
页码：6804 / 6810
页数：7
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