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

被引：29

作者：

Carreño, MC ^{[1
]}

Merino, E ^{[1
]}

Ribagorda, M ^{[1
]}

Somoza, A ^{[1
]}

Urbano, A ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol050287a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1419 / 1422

页数：4

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