C-去甲-D-高甾烷甾体生物碱ABC环的合成:环巴胺的全合成研究

Synthesis of A B C-ring subunit of C-nor-D-homo-steroidal alkaloids:towards the total synthesis of cyclopamine

摘要: 本研究工作建立了一种合成环巴胺ABC环的有效方法。该方法的亮点在于扁桃酸缩醛介导的稠环酮(±)-4的拆分及IBX-介导的化合物12的多位点同步氧化。所建立的光学纯关键中间体(+)-4和2的简便合成方法为进一步合成具有生物活性的各种C-去甲-D-高甾烷甾体生物碱(如环巴胺)提供了可行性。

Abstract: A practical approach to the synthesis of the A,B and C-ring subunit of cyclopamine has been developed.This synthetic tactic highlights the utility of mandelate acetal-mediated resolution of the fused ring ketone(±)-4 and IBX-mediated oxidation cascades from 12 to 9.The availability of advanced intermediates from enantiomerically pure(+)-4 and 2 could provide efficient access to biologically active and structurally diverse C-nor-D-homo-steroidal alkaloids such as cyclopamine.