A STEREODIVERGENT ACCESS TO NATURALLY-OCCURRING AMINOCARBASUGARS FROM (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - TOTAL SYNTHESIS OF PENTA-N,O-ACETYL-(+/-)-VALIDAMINE AND ITS C-1 AND C-2 STEREOISOMERS

被引：45

作者：

ACENA, JL ^{[1
]}

ARJONA, O ^{[1
]}

DELAPRADILLA, RF ^{[1
]}

PLUMET, J ^{[1
]}

VISO, A ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,E-28006 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total syntheses of the antibiotic component validamine 1 and its three diastereomers 2-4 have been accomplished as their racemic penta-N,O-acetates via stereocontrolled nucleophilic epoxidation of polyhydroxylated cyclohexenyl sulfones, obtained from (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptanes. The diastereoselectivity of the epoxidation can be readily controlled by careful choice of the hydroxyl protecting groups. Ring opening of the resulting alpha,beta-epoxy sulfones followed by stereocontrolled introduction of an amine precursor led to the four C-1 and C-2 diastereomers of 1-aminocarbasugars.

引用

页码：6419 / 6424

页数：6