+/--3'-DEOXYARAARISTEROMYCIN VIA A SURPRISING REARRANGEMENT

被引：6

作者：

FRICK, W ^{[1
]}

PATIL, SD ^{[1
]}

GAMBINO, AJ ^{[1
]}

SCHNELLER, SW ^{[1
]}

机构：

[1] UNIV S FLORIDA,DEPT CHEM,TAMPA,FL 33620

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(00)73876-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrolysis of (+/-)-3beta-acetoxy-4alpha-benzamido-1alpha-cyclopentanemethyl acetate (5) with 6 N hydrochloric acid has been found to give an amine in which the configuration at C-3 has been inverted. This conclusion was reached following conversion of the amine into (+/-)-3'-deoxyaraaristeromycin (8) by following a standard adenine formation process of (i) reaction with 5-amino-4,6-dichloropyrimidine, (ii) ring closure with diethoxymethyl acetate, and (iii) ammonolysis. Use of basic hydrolysis conditions with 5 led to the expected (+/-)3'-deoxyaristeromycin (7).

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页码：5541 / 5544

页数：4

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