Stereoselective formation of tri- and tetracycles by samarium diiodide-induced cyclizations of naphthyl-substituted ketones

被引：32

作者：

Berndt, M ^{[1
]}

Hlobilová, I ^{[1
]}

Reissig, HU ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem, D-14195 Berlin, Germany

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 06期

关键词：

D O I：

10.1021/ol036456d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium diiodide promotes smooth reductive cyclizations of gamma-naphthyl-substituted ketones to afford tri- and tetracyclic compounds in high yields and with excellent stereoselectivities. Cyclic ketones furnish steroid-like compounds with "unnatural" cis/cis annulation of rings B/C/D. The remaining styrene-type double bond of ring B allows further stereoselective reactions. Cases with matched and mismatched relative configuration could be identified leading to dramatic differences in the ring closure ability.

引用

页码：957 / 960

页数：4

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