TOTAL SYNTHESIS OF THE GASTROPROTECTIVE SUBSTANCE AI-77-B AND OF ANALOGS

被引：30
作者：
DURGNAT, JM [1 ]
VOGEL, P [1 ]
机构：
[1] UNIV LAUSANNE,CHIM SECT,RUE BARRE 2,CH-1005 LAUSANNE,SWITZERLAND
来源：
HELVETICA CHIMICA ACTA | 1993年 / 76卷 / 01期
关键词：
D O I：
10.1002/hlca.19930760116
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The Diels-Alder adducts 8 of furan to 1-cyanovinyl acetate were converted into (methyl 3-chloro-5-043-chlorobenzoyl)-2,3-dideoxy-alpha-DL-arabino-hexofuranosid)uronic acid ((+/-)-18a) and into (methyl 3-azido-5-0-(3-chlorobenzoyl)-2,3-dideoxy-alpha-DL-ribo-hexofuranosid)uronic acid ((+/-)-41a). These compounds were condensed to (3S)-3-[(1'S)-1'-amino-3'-methylbutyl]-3,4-dihydro-8-hydroxyisocoumarin hydrochloride ((-)-2); the resulting mixtures of diastereoisomeric amides were transformed and separated to give the gastroprotective substance AI-77-B ((-)-1) and analogues.
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页码：222 / 240
页数：19
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