Trimethylsilyltriflate-promoted addition of 2-trimethylsilyloxyfuran to a chiral cyclic nitrone;: a short synthesis of [1S(1α,2β,7β,8α,8aα)]-1,2-di(t-butyldiphenylsilyloxy)-indolizidine-7,8-diol

被引：21

作者：

Lombardo, M ^{[1
]}

Trombini, C ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 02期

关键词：

2-trimethylsilyloxyfuran; (3S,4S)-3,4-dihydro-3,4-di(t-butyldiphenylsilyloxy)-2H-pyrrole 1-oxide; 4S(4 alpha,5 beta,5 alpha beta,5b alpha,8a alpha)]-hexahydro-4,5-di(t-butyldiphenylsilyloxy)-pyrrolo [1,2-b]furo[2,3-d] isoxazol-7(3H)one;

D O I：

10.1016/S0040-4020(99)01001-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trimethylsilyl triflate promoted addition of 2-trimethylsilyloxyfuran to (3S,4S)-3,4-dihydro- 3,4-di(t-butyldiphenylsilyloxy)-2H-pyrrole 1-oxide, derived from (R,R)-tartaric acid, displays complete facial selectivity, affording two diastereomeric butenolides in excellent overall yield. The major adduct undergoes silica-gel induced ring-closure to give in almost quantitative yield [4S(4 alpha,5 beta,5a beta,5b alpha,8a alpha)]-hexahydro-4,5-di(t-butyldiphenylsilyoxy)-pyrrolo [1,2-b]furo[2,3d] isoxazol-7(3H)one; reduction with DIBAH followed by hydrogenolysis on Pd(OH)(2)/C affords the partially protected 1,2,7,8-indolizidinetetrol. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：323 / 326

页数：4

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