A Pauson-Khand approach to the synthesis of ingenol.

A Pauson-Khand approach to the synthesis of ingenol.
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DOI:
10.1021/ol050103s
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发表时间:
2005-03
期刊:
影响因子:
5.2
通讯作者:
J. Winkler;Esther C Y Lee;L. I. Nevels
J. Winkler;Esther C Y Lee;L. I. Nevels
中科院分区:
化学1区
文献类型:
--
作者:
J. Winkler;Esther C Y Lee;L. I. Nevels

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[reaction: see text] Pauson-Khand cyclization of dioxanone photoadduct 21 leads to the formation of a single product in good yield. However, retro-aldol fragmentation of the pentacyclic cyclopentenone 22 leads to the formation of 23, with cis C-8/C-10 intrabridgehead stereochemistry, unlike the target compound ingenol 1, which possesses C-8/C-10 trans intrabridgehead stereochemistry.