期刊
TETRAHEDRON
卷 65, 期 1, 页码 212-220出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.10.070
关键词
Chiral version of the Burgess reagent; Vinyloxiranes; Vinylaziridines; Enzymatic dihydroxylation of aromatics; Reductive amination; trans-Amino alcohols; Balanol; Enantiodivergent synthesis
资金
- Natural Science and Engineering Research Council (NSERC)
- TDC Research Foundation
- Canada Foundation for Innovation (CFI)
- Ontario Innovation Trust (OIT)
- Research Corporation
- TDC Research, Inc.
- Brock University
Formal total syntheses of both enantiomers of balanol have been achieved by the preparation of the protected hexahydroazepine core 2. Two complementary routes have been investigated. The first relied on the regioselective opening of 1,2-epoxycyclohex-3-ene with a chiral-auxiliary version of the Burgess reagent to provide a diastereomeric pair of cis-fused cyclic sulfamidates. The sulfamidates were transformed to trans-amino benzoates with ammonium benzoate and, after separation, converted to (-)-2 and (+)-2 by oxidative cleavage and reductive amination. The second approach utilized vinylaziridines derived from 1-bromo-2,3-dihydroxycyclohexa-4,6-diene obtained by the whole-cell fermentation of bromobenzene with Escherichia coli JM109(pDTG601). Stereoselective opening of the aziridines generated the requisite trans-amino alcohol derivatives, which after saturation of the vinyl bromide moieties were converted to (-)-2 and (+)-2 by oxidative cleavage of the cis-diol and reductive amination. Experimental and spectral data are provided for all new compounds. (C) 2008 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据