Stereoselective synthesis of tetrahydrofuran lignans via BF3•OEt2-promoted reductive deoxygenation/epimerization of cyclic hemiketal:: Synthesis of (-)-odoratisol C, (-)-futokadsurin A, (-)-veraguensin, (+)-fragransin A2, (+)-galbelgin, and (+)-talaumidin

被引：45

作者：

Kim, Hyoungsu ^{[1
]}

Wooten, Ceshea M. ^{[1
]}

Park, Yongho ^{[1
]}

Hong, Jiyong ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 20期

关键词：

DIVERGENT DIASTEREOSELECTIVITY; STEREOCHEMICAL CONFIRMATION; NUCLEOPHILES; NEOLIGNANS; ATTACK; MODEL;

D O I：

10.1021/ol7016388

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

[GRAPHICS] A versatile route to the synthesis of 2,5-diaryl-3,4-dimethyltetrahydrofuran lignans, (-)-odoratisol C (1), (-)-futokadsurin A (2), (-)-veraguensin (3), (+)-fragransin A(2) (4), (+)-galbelgin (5), and (+)-talaumidin (6), is described. Central to the synthesis of the lignans is BF3 center dot OEt2-promoted deoxygenation/epimerization of the hemiketal 9a followed by stereoselective reduction of the oxocarbenium ion intermediates 8a,b.

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页码：3965 / 3968

页数：4

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