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C-去甲-D-同甾体生物碱的 A、B、C 环亚单位的合成:向环巴胺的全合成迈进。

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

机构信息

Center for Drug Discovery, College of Pharmacy, China Pharmaceutical University, Nanjing, China.

出版信息

Chin J Nat Med. 2013 May;11(3):277-83. doi: 10.1016/S1875-5364(13)60029-1.

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.

摘要

已经开发出一种实用的合成氨甲酰环巴胺的 A、B 和 C 环亚单位的方法。这种合成策略突出了扁桃酸缩醛介导的稠环酮(±)-4 的拆分和 IBX 介导的从 12 到 9 的氧化级联反应的实用性。从对映体纯的(+)-4 和 2 获得的高级中间体可以有效地获得具有生物活性和结构多样性的 C-去甲-D-同甾体生物碱,如氨甲酰环巴胺。

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