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
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D O I：
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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.
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页码：2631 / 2637
页数：7
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