Asymmetric total synthesis of (-)-podophyllotoxin

被引:35
作者
Bush, EJ
Jones, DW
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 02期
关键词
D O I
10.1039/p19960000151
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(-)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels-Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(-)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.
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页码:151 / 155
页数:5
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