Convergent route to the purpuromycin bisphenolic spiroketal: hydrogen bonding control of spiroketalization stereochemistry

被引：36

作者：

Waters, Stephen P. ^{[1
]}

Fennie, Michael W. ^{[1
]}

Kozlowski, Marisa C. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 30期

关键词：

D O I：

10.1016/j.tetlet.2006.05.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient [3+2] nitrile oxide/olefin cycloaddition provided a rapid and convergent entry into precursors of bisphenolic spiroketals, a structural type unique to the rubromycin family of natural products. In addition, implementation of the premise that a hydrogen bond from the C4-OH controls the stereochemistry of the purpuromycin core resulted in moderate diastereocontrol in the spiroketalization. Spectroscopic and X-ray data of these systems have provided the first assignment of the relative configuration of purpuromycin. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5409 / 5413

页数：5

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