Synthesis of the first "inside-outside" eight-membered ring via ring-closing metathesis: A total synthesis of (+/-)-asteriscanolide

被引：0

作者：

Krafft, ME ^{[1
]}

Cheung, YY ^{[1
]}

Juliano-Capucao, CA ^{[1
]}

机构：

[1] Florida State Univ, Dept Chem, Tallahassee, FL 32306 USA

来源：

SYNTHESIS-STUTTGART | 2000年 / 07期

关键词：

ring-closing; metathesis; total synthesis; Pauson-Khand cycloaddition; transition metal mediated reactions;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+/-)-asteriscanolide which features two transition metal-mediated carbocyclic ring forming reactions as key elements of our strategy (Scheme 1) is described. The highly functionalized cyclopentenone 4, the product of a cobalt-mediated Pauson-Khand [2+2+1]cycloaddition, is the key starting point for the synthesis. Excellent regiocontrol was obtained in the intermolecular Pauson-Khand reaction. Further synthetic manipulations of 4 led to diene 16 which underwent ring-closing metathesis using (PPh3)(2)Cl2Ru(CHPh)] to provide the desired 'inside-outside' tricycle 17. Conversion of 17 to 1 was achieved in a minimal number of steps. The synthesis of asteriscanolide has been achieved in 19 steps and 12 % overall yield.

引用

页码：1020 / 1026

页数：7

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