GENERAL CONJUGATE-ADDITION METHOD FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE LIGNANS - TOTAL SYNTHESIS OF (-)- AND (+)-BURSERAN, (-)-DEHYDROXYCUBEBIN, (-)-TRICHOSTIN, (-)-CUBEBIN, (-)-5''-METHOXYHINOKININ, AND (-)-HINOKININ

被引：55

作者：

REHNBERG, N ^{[1
]}

MAGNUSSON, G ^{[1
]}

机构：

[1] UNIV LUND, LUND INST TECHNOL, CTR CHEM, BOX 124, S-22100 LUND, SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 14期

关键词：

D O I：

10.1021/jo00301a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition of benzylic diphenyldithioacetal anions to enantiomerically pure (-)-(2i?)- and (+)-(2S)-2-(benzyloxy)-2,5-dihydro-4-[3,4-(methylenedioxy)benzoyl]furan (2r and 2s) gave complete lignan skeletons of the dibenzylbutane class. Desulfurization followed by hydrogenolysis and, when appropriate, oxidation gave the title enantiomerically pure (>99% ee) lignans 45–50 in 24-35% overall yields from 2r and 2s. © 1990, American Chemical Society. All rights reserved.

引用

页码：4340 / 4349

页数：10

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