PRODUCTS FROM FURANS .11. TOTAL SYNTHESIS OF 4-(D-ALANYLAMINO)-2-AMINO-2,3,4-TRIDEOXY-DL-THREO-PENTOSE (3-DEOXY-DL-PRUMYCIN)

被引：14

作者：

CONSTANTINOUKOKOTOU, V

COULADOUROS, EA

GEORGIADIS, MP

KOKOTOS, G

GEORGIADIS, TM

机构：

[1] AGR UNIV ATHENS,CHEM LABS,IERA ODOS 75,GR-11855 ATHENS,GREECE

[2] UNIV ATHENS,DEPT CHEM,ATHENS,GREECE

[3] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

CARBOHYDRATE RESEARCH | 1991年 / 222卷

关键词：

D O I：

10.1016/0008-6215(91)89015-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

3-Deoxy-DL-prumycin (1) was synthesized from 2-furanmethanol (2-furfuryl alcohol, 2) in eleven steps in 15% total yield. Michael addition of azide anion to 2,3-dideoxy-DL-pent-2-enopyranos-4-ulose (3) and reduction in situ of the adduct afforded the key intermediates 5 and 6. Introduction of a second azido group with inversion of configuration at C-4 afforded intermediates 14 and 17, both of which had a threo configuration in regard to C-2 and C-4. Coupling with D-alanine and total deprotection yielded the title compound 1.

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页码：163 / 172

页数：10

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