A short and convenient access to a trans-hydrindane unit from the anti-meso-acetylmethyldivinylcyclopentane via a radical pathway

被引：11

作者：

Chapelon, AS ^{[1
]}

Ollivier, C ^{[1
]}

Santelli, M ^{[1
]}

机构：

[1] Univ Paul Cezanne, Fac Sci & Tech St Jerome, Synth Organ Lab, Associe CNRS,UMR 6180, F-13397 Marseille 20, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 16期

关键词：

D O I：

10.1016/j.tetlet.2006.02.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route for multigram synthesis of a trans-hydrindane unit, involving a selective 6-endo-trig alpha-carbonyl radical cyclization of the alpha-xanthyl ketone 10 derivating from the anti-meso-acetylmethyldivinylcyclopentane 9 through a xanthate group transfer, is achieved in good yield. Preparation of an advanced intermediate for the Julia-Kocienski Coupling, used in the elaboration of the trienic system of vitamin D (or calciferol) analogs, was materialized by conversion of the xanthate moiety to a 2-benzothiazole sulfonyl group. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2747 / 2750

页数：4

共 44 条

[1]

AKHREM AA, 1970, TOTAL STEROID SYNTHE

[2] CONFORMATIONAL-ANALYSIS .80. HYDRINDANONE RING-SYSTEM [J].