Synthesis of (±)-secosyrin 1 and a formal synthesis of (-)-secosyrin 1

被引：18

作者：

Donohoe, TJ

Fisher, JW

Edwards, PJ

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[2] Pfizer Global R&D, Sandwich Labs, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 04期

关键词：

D O I：

10.1021/ol0362313

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthesis of (+/-)-secosyrin 1 is presented that starts from an electron-deficient furan; reductive alkylation under Birch conditions gives rapid access to the natural product skeleton. Two aspects of stereoselectivity are explored, the first being directed dihydroxylation of a homoallylic alcohol. Second, the facial selectivity obtained during reduction of a highly substituted cyclic ketone was examined. Finally, our synthesis was rendered enantioselective by the reduction of a furan bearing a chiral auxiliary.

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页码：465 / 467

页数：3

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