A NEW ASYMMETRIC-SYNTHESIS OF (S)-DOLAPHENINE AND ITS HETEROAROMATIC CONGENERS UTILIZING (+)-2-HYDROXY-3-PINANONE AND (-)-3-HYDROXY-2-CARANONE AS CHIRAL AUXILIARIES

被引：43

作者：

IRAKO, N ^{[1
]}

HAMADA, Y ^{[1
]}

SHIOIRI, T ^{[1
]}

机构：

[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN

来源：

TETRAHEDRON | 1995年 / 51卷 / 46期

关键词：

D O I：

10.1016/0040-4020(95)00828-V

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-2-Hydroxy-3-pinanone ((+)-HyPN, (+)-2a) and (-)-3-hydroxy-2-caranone ((-)-2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2-thiazolyl)methyiamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (-)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27a-d.

引用

页码：12731 / 12744

页数：14

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