Total synthesis of (±)-bruguierol A via an intramolecular [3+2] cycloaddition of cyclopropane 1,1-diester

被引：46

作者：

Hu, Bao ^{[1
]}

Xing, Siyang ^{[1
]}

Ren, Jun ^{[1
]}

Wang, Zhongwen ^{[1
]}

机构：

[1] Nankai Univ, Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 30期

基金：

中国国家自然科学基金;

关键词：

Bruguierol; Total synthesis; Nature product; Cycloaddition; Cyclopropane; FRIEDEL-CRAFTS ALKYLATION; EXPEDITIOUS SYNTHESIS;

D O I：

10.1016/j.tet.2010.05.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of natural product (+/-)-bruguierol A was accomplished in 10-steps and with an overall 16.8% yield. The embedded unique 8-oxabicyclo[3.2.1]octane core skeleton in this natural product was constructed via a novel Sc(OTf)(3)-catalyzed intramolecular [3+2] cycloaddition of cyclopropane, which was developed recently in this laboratory. This general synthetic strategy can be potentially applied to the synthesis of a broad range of structurally related natural products. (C) 2010 Elsevier Ltd. All rights reserved.

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页码：5671 / 5674

页数：4

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