Total synthesis of (±)-haouamine A

Total synthesis of (±)-haouamine A
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DOI:
10.1021/ja0602997
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发表时间:
2006-03-29
影响因子:
15
通讯作者:
Burns, NZ
Burns, NZ
中科院分区:
化学1区
文献类型:
--
作者:
Baran, PS;Burns, NZ

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首次报道了高度复杂和有效的抗癌药物haouamine A的全合成,通过八步序列。序列的简洁性和化学,位置和立体选择性(平面和轴向手性)的完全控制是可能的,通过发明的化学专门针对手头的问题,即级联成环过程中通过迄今未知的化学实体的茚并-四氢吡啶环系统,以及一个吡喃酮辅助缝合令人生畏的芳香环。
The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.