An Enantiospecific Polyene Cyclization Initiated by an Enantiomerically Pure Bromonium Ion

被引：14

作者：

Braddock, D. Christopher ^{[1
]}

Marklew, Jared S. ^{[1
]}

Foote, Kevin M. ^{[2
]}

White, Andrew J. P. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

[2] AstraZeneca, Macclesfield, Cheshire, Uruguay

来源：

CHIRALITY | 2013年 / 25卷 / 11期

基金：

英国工程与自然科学研究理事会;

关键词：

bromonium ion; polyene cyclization; enantiospecific; MARINE NATURAL-PRODUCTS; ENANTIOSELECTIVE BIOMIMETIC CYCLIZATION; BIOGENETIC-TYPE SYNTHESIS; BROMINATIVE CYCLIZATION; CATIONIC POLYCYCLIZATIONS; ASYMMETRIC BROMONIUM; APLYSIA-KURODAI; LAURENCIA; ACIDS; HALOCYCLIZATION;

D O I：

10.1002/chir.22194

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Dimethylaluminum triflate-mediated activation of tetrafluorobenzoates of enantiomerically pure bromohydrins results in enantiospecific polyene cyclizations. The initiation of cyclization by enantiomerically pure bromonium ions and subsequent propagation is not subject to catastrophic erosion of enantiomeric purity by any intramolecular or intermolecular bromonium ion-to-alkene transfer. Chirality 25:692-700, 2013. (c) 2013 Wiley Periodicals, Inc.

引用

页码：692 / 700

页数：9

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