Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1-C10 fragment

被引：6

作者：

Kommana, Praveen ^{[1
]}

Chung, Seung Won ^{[1
]}

Donaldson, William A. ^{[1
]}

机构：

[1] Marquette Univ, Dept Chem, Milwaukee, WI 53201 USA

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 43期

关键词：

D O I：

10.1016/j.tetlet.2008.08.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R*,4R*,6R*,7S*,8R*,10S* relative configuration. (C) 2008 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6209 / 6211

页数：3

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