Synthesis of trans-syn-trans fused bis-pyrans via endo-selective cyclizations of cyclic sulfates

被引：11

作者：

McDonald, FE ^{[1
]}

Vadapally, P ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(99)00214-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid-catalyzed cyclization of hydroxy-cyclic sulfates occurs with endo-regioselectivity affording bispyran products from substrates in which the nucleophilic hydroxyl and electrophilic cyclic sulfate groups are 1,2-trans-substituted on a cyclic pyran template. This methodology is demonstrated in an enantioselective synthesis of the trans-syn-trans fused AB cyclic ether rings of the brevetoxin natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：2235 / 2238

页数：4

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