3-烷基-2-芳基四氢呋喃-4-醇的立体选择性合成：(±)-泡桐宁的全合成
Stereoselective synthesis of 3-alkyl-2-aryltetrahydrofuran-4-ols: total synthesis of (+/-)-paulownin.
作者信息
Angle Steven R, Choi Inchang, Tham Fook S
机构信息
Department of Chemistry, Wright State University, Dayton, Ohio 45435, and Department of Chemistry, University of California, Riverside, California 92521, USA.
出版信息
J Org Chem. 2008 Aug 15;73(16):6268-78. doi: 10.1021/jo800901r. Epub 2008 Jul 23.
PMID:18646863
Abstract
A formal [3 + 2]-cycloaddition involving the Lewis acid mediated reaction of alpha-silyloxy aldehydes and styrenes to afford 3-alkyl-2-aryltetrahydrofuran-4-ols has been developed. This methodology was applied to the total synthesis of the naturally occurring furofuran lignan (+/-)-paulownin.
摘要
已开发出一种正式的[3 + 2]环加成反应，该反应涉及路易斯酸介导的α-硅氧基醛与苯乙烯的反应，以生成3-烷基-2-芳基四氢呋喃-4-醇。该方法已应用于天然呋喃呋喃木脂素（±）-泡桐素的全合成。
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