ALPHA-AMINO ALDEHYDE EQUIVALENTS AS SUBSTRATES FOR RABBIT MUSCLE ALDOLASE - SYNTHESIS OF 1,4-DIDEOXY-D-ARABINITOL AND 2(R),5(R)-BIS(HYDROXYMETHYL)-3(R),4(R)-DIHYDROXYPYRROLIDINE

被引：92

作者：

HUNG, RR ^{[1
]}

STRAUB, JA ^{[1
]}

WHITESIDES, GM ^{[1
]}

机构：

[1] HARVARD UNIV, DEPT CHEM, CAMBRIDGE, MA 02138 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 12期

关键词：

D O I：

10.1021/jo00012a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work examined the application of rabbit muscle aldolase (RAMA) to stereospecific carbon-carbon bond formation in the preparation of carbohydrates containing amino groups. Several alpha-amino aldehyde equivalents were evaluated as substrates for RAMA and for their synthetic utility in transformations following the aldol reaction. This methodology is illustrated by the syntheses of the pyrrolidine alkaloids 1,4-dideoxy-D-arabinitol and 2(R),5(R)-bis(hydroxymethyl)-3(R), 4(R)-dihydroxypyrrolidine. The kinetic resolution of racemic aldehydes by RAMA and mild methods for transforming the amino equivalents into the desired amines are discussed briefly.

引用

页码：3849 / 3855

页数：7

共 45 条

[1] IODOSYLBENZENE-TRIMETHYLSILYL AZIDE-BORON TRIFLUORIDE ETHERATE - A HIGHLY EFFICIENT SYSTEM FOR DIRECT SYNTHESIS OF ALLYL AZIDES FROM ALLYLSILANES [J].