ASYMMETRIC TOTAL SYNTHESIS OF NATURALLY-OCCURRING (R)-(-)-ENANTIOMER OF TYLOPHORINE VIA INTRAMOLECULAR DOUBLE MICHAEL REACTION

被引：36

作者：

IHARA, M ^{[1
]}

TAKINO, Y ^{[1
]}

TOMOTAKE, M ^{[1
]}

FUKUMOTO, K ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,AOBAYAMA,SENDAI 980,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 08期

关键词：

D O I：

10.1039/p19900002287

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric total synthesis of the naturally occurring (R)-(-)-enantiomer (1) of tylophorine was achieved with high enantioselectivity via the intramolecular double Michael reaction of α,β-unsaturated esters (10) and (20), having two different chiral auxiliaries, with t-butyldimethylsilyl trifluoromethanesulphonate in the presence of triethylamine. (-)-Phenylmenthol and (2R,4S,5R)-(-)-4-(t- butyldimethylsiloxymethyl)-5-hydroxy-2-phenyl-1,3-dioxane, readily available from D-glucose, were used as chiral auxiliaries.

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页码：2287 / 2292

页数：6

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