ENANTIOSELECTIVE SYNTHESIS OF (+)-O-TRIMETHYLSAPPANONE-B AND (+)-O-TRIMETHYLBRAZILIN

被引：49

作者：

DAVIS, FA

CHEN, BC

机构：

[1] Department of Chemistry, Drexel University, Philadelphia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 07期

关键词：

D O I：

10.1021/jo00059a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The homoisoflavanoid (+)-O-trimethylbrazilin (1b) was prepared in 70% yield and 92% ee by acid-catalyzed rearrangement of O-trimethylsappanol (8) prepared by reduction of (R)-(-)-O-trimethylsappanone B (2b). The key step in the synthesis of (R)-(-)-2b is the reagent-controlled highly enantioselective hydroxylation (94%) of the sodium enolate of (+/-)-4-chromanone (3b) with the (+)-8,8-dichlorocamphorsulfonyl oxaziridine 7b.

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页码：1751 / 1753

页数：3

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