作者:Edward J. Bush、David W. Jones
DOI:10.1039/p19960000151
日期:——
(–)-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.
已通过八个步骤合成了光学纯度为98%的(-)-鬼臼毒素,总产率为15%。关键步骤是Diels–Alder向手性亲二烯体5 [5-]中添加邻醌类吡喃酮2 [6,7-亚甲基二氧基-1-(3,4,5-三甲氧基苯基)-2-苯并吡喃-3-酮] (-)-薄荷酰呋喃-2(5 H)-一],具有很高的区域,内部和面部选择性。