Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary

被引：56

作者：

Abiko, A ^{[1
]}

Masamune, S ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 07期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/0040-4039(95)02353-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric alkylation of the potassium enolates derived from N-propionyl benzopyrano[4,3-c]-isoxazolidine derivatives with chiral alkyl triflates proceeded smoothly with high diastereoselectivity. The stereochemistry of the newly formed stereogenic center was fully controlled by the facial selectivity of the enolate according to the rule of double asymmetric synthesis. The application of this methodology led to the first synthesis of (+)-siphonarienone, a marine polypropionate natural product.

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页码：1081 / 1084

页数：4

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