ASYMMETRIC-SYNTHESIS OF LIGNANS OF THE DIBENZYLBUTANEDIOL AND TETRAHYDRODIBENZOCYCLOOCTENE SERIES

被引：0

作者：

PELTER, A ^{[1
]}

WARD, RS ^{[1
]}

JONES, DM ^{[1
]}

MADDOCKS, P ^{[1
]}

机构：

[1] WELLCOME FDN LTD,DARTFORD DA1 5AH,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 21期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enolate anions obtained by conjugate addition to (-)-5-(1-menthyloxy)furan-2(5H)-one are quenched with benzyl bromides or iodides to yield homochiral dibenzylbutyrolactones. Desulfurisation followed by lithium aluminium hydride reduction affords homochiral 2,3-dibenzylbutane-1,4-diols, including (-)-dimethylsecoisolariciresinol and (-)-dihydroclusin. Desulfurisation followed by reduction with NaBH4/KOH gives the homochiral 2,3-dibenzylbutyrolactones (-)-dimethylmatairesinol, (-)-kusunokinin and (-)-yatein, which undergo stereoselective oxidative coupling with DDQ in trifluoroacetic acid to give homochiral tetrahydrodibenzocyclooctene lignans belonging to the isostegane series.

引用

页码：2631 / 2637

页数：7

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