A Novel Cis-Selective Cyclohexanone Annulation as the Key Step of a Total Synthesis of the Sesquiterpene Isoacanthodoral

被引：12

作者：

Hampel, Thomas ^{[1
]}

Brueckner, Reinhard ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 21期

关键词：

DIELS-ALDER REACTIONS; ALDEHYDES; KETONES; CONVERSION;

D O I：

10.1021/ol9018979

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Isoacanthodoral (1) is a structurally unique sesquiterpene in that it is a bicyclo[4.4.0]dec-1-ene with a cis-rather than the common trans-junction between the constituting rings. An efficient construction of this motif has been accomplished by a novel cis-selective cyclohexanone annulation, combining the lithium enolate of ester 8, the alpha,beta-unsaturated ester 6, and vinylmagnesium bromide in a single synthetic operation. For completing the total synthesis of 1, a Shapiro-olefination/hydrogenation sequence and a reductive cyanation were employed.

引用

页码：4842 / 4845

页数：4

共 45 条

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