STEREOCONTROLLED SYNTHESES OF (-)-GONIOFUFURONE AND (-)-8-EPI-GONIOFUFURONE

被引:31
作者
SHING, TKM
TSUI, HC
ZHOU, ZH
机构
[1] Department of Chemistry, The Chinese University of Hong Kong, Shatin
关键词
D O I
10.1016/S0040-4020(01)89441-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute configurations of natural goniolufurone and 8-epi-goniofufurone are shown to be 2 and 4 respectively by unambiguous syntheses of their enantiomers 1 and 3 from D-glycero-D-gulo-heptono-gamma-lactone 7 involving an intramolecular Michael reaction as the key step. The diol 6, readily available from D-glycero-D-gulo-heptono-gamma-lactone, has been converted by six sequential reactions (acetylation, hydrolysis, deacetylation, glycol cleavage, Wittig reaction, and hydrolysis) into the gamma-lactone 5 which underwent an intramolecular Michael reaction to yield (-)-goniofufurone 1. Likewise reactions of the monoacetate 12 gave (-)-8-epi-goniofufurone 3.
引用
收藏
页码:8659 / 8666
页数:8
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