Stereoselective total synthesis of the tricyclic sesquiterpene (±)-kelsoene by an intramolecular Cu(I)-catalyzed [2+2]-photocycloaddition reaction

被引：22

作者：

Bach, T ^{[1
]}

Spiegel, A ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany

来源：

SYNLETT | 2002年 / 08期

关键词：

cycloadditions; photochemistry; ring closure; terpenoids; total synthesis;

D O I：

10.1055/s-2002-32972

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sesquiterpene kelsoene (1) has been stereoselectively prepared starting from the known 1,2,3-trisubstituted cyclopentane 7 in 14 synthetic operations. The intramolecular Cu(I)-catalyzed photocycloaddition of the precursor 10 which proceeded in 89% yield established the relative configuration of the two stereogenic centers (C-1, C-8) within the cyclobutane ring. The stereochemistry at C-6 was adjusted by the stereoselective hydrogenation of the unsaturated enone 15.

引用

页码：1305 / 1307

页数：3

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