Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones

Rapid access to the welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones
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DOI:
10.1021/ol051239t
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发表时间:
2005-09-15
期刊:
影响因子:
5.2
通讯作者:
Simpkins, NS
Simpkins, NS
中科院分区:
化学1区
文献类型:
--
作者:
Baudoux, J;Blake, AJ;Simpkins, NS

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通过酸介导的适当取代的吲哚醛的环闭合,建立了非常快速地获得环己酮桥连的吲哚系统,这涉及到一个明显的羟醛类中间体的缩合。桥连吲哚中间体之一被进一步转化成具有Welwitindolinone生物碱的基本骨架的羟吲哚。
A very rapid access to cyclohexanone-bridged indole systems was established by an acid-mediated ring closure of appropriately substituted indole aldehydes, which involved an apparent disproportionation of an aldol-like intermediate. One of the bridged indole intermediates was further transformed into an oxindole having the essential skeleton of the Welwitindolinone alkaloids.