STUDIES RELATED TO ANTHRACYCLINES .3. STEREOSELECTIVE SYNTHESIS OF (+)-DAUNOMYCINONE

被引：11

作者：

EDWARDS, WD ^{[1
]}

GUPTA, RC ^{[1
]}

RAYNOR, CM ^{[1
]}

STOODLEY, RJ ^{[1
]}

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,POB 88,MANCHESTER M60 1QD,LANCS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 08期

关键词：

D O I：

10.1039/p19910001913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound 2b was prepared by a seven-step sequence from (+/-)-4a,9a-epoxy-4a,9a-dihydro-5-methoxyanthracene-1,4,9,10-tetraone 3b/3c and (E)-1-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-trimethylsilyloxybuta-1,3-diene 4. Acidic hydrolysis of the crude Diels-Alder cycloadducts of compounds 3b/3c and 4 led, after fractional crystallisation, to the isolation of (5aS,6aR,7S,10aR,11aR)-5a,11a-epoxy-4-methoxy-5a,6a,7,8,9,10,10a,11a-octahydro-7-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)naphthacene-5,6,9,11,12-pentaone 6b. The last-cited compound was transformed into (+)-daunomycinone 2b by reduction, ethynylation, oxidation, hydrolysis and hydration steps.

引用

页码：1913 / 1918

页数：6

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