ENANTIOSPECIFIC SYNTHESES OF ARISTEROMYCIN AND NEPLANOCIN-A

被引：71

作者：

WOLFE, MS ^{[1
]}

ANDERSON, BL ^{[1
]}

BORCHERDING, DR ^{[1
]}

BORCHARDT, RT ^{[1
]}

机构：

[1] UNIV KANSAS,DEPT MED CHEM,LAWRENCE,KS 66045

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 15期

关键词：

D O I：

10.1021/jo00302a043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The carbocyclic nucleosides (-)-aristeromycin and (-)-neplanocin A were made enantiospecifically in nine steps and ten steps, respectively, from D-ribonic acid γ-lactone. Quenching of an organocuprate conjugate addition reaction with either acetic acid or methanesulfinyl chloride determines whether the divergent synthetic route branches toward (-)-aristeromycin or (-)-neplanocin A. An alternate synthesis of cyclopen ten one 1, a common intermediate to these compounds, from D-gulonic acid 7-lactone is also described. © 1990, American Chemical Society. All rights reserved.

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页码：4712 / 4717

页数：6

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