(+)-和(-)-二氢表埃坡福明以及(+)-表埃坡福明的对映选择性合成。

Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin.

作者信息

Carreño M Carmen, Merino Estíbaliz, Ribagorda María, Somoza Alvaro, Urbano Antonio

机构信息

Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.

出版信息

Org Lett. 2005 Mar 31;7(7):1419-22. doi: 10.1021/ol050287a.

DOI:10.1021/ol050287a

PMID:15787521

Abstract

[reaction: see text] The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality, previous to oxidation of the beta-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone.

摘要

[反应：见正文] 分别从（对甲苯基亚磺酰基）甲基对苯二酚（SR）-或（SS）-3和（4R，SR）-4实现了二氢表埃坡福明（1）和（+）-表埃坡福明（2）两种对映体的对映选择性合成。关键特征包括在将高级中间体的β-羟基亚砜部分氧化为相应砜之前，AlMe₃对苯二酚3进行立体控制的共轭加成以及向酮官能团的逆缩合反应。