Alkene-Alkyne Coupling as a Linchpin: An Efficient and Convergent Synthesis of Amphidinolide P
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- 作者：Barry M. Trost and Julien P. N. Papillon
- 刊名：Journal of the American Chemical Society
- 出版年：2004
- 出版时间：October 27, 2004
- 年：2004
- 卷：126
- 期：42
- 页码：13618 - 13619
- 全文大小：57K
- 年卷期：v.126,no.42(October 27, 2004)
- ISSN：1520-5126
文摘
A short and efficient synthesis of the cytotoxic macrolide amphidinolide P is described. A remarkably chemo- and regioselective ruthenium-catalyzed alkene-alkyne coupling allows for a convergent synthesis and demonstrates that both enynes and 
-lactones are suitable coupling partners. This work also features a novel strategy for the preparation of macrolactones via intramolecular transesterification of -lactones. The target structure was prepared in 15 steps for the longest linear sequence and 10% overall yield, 24 steps total.
-lactones are suitable coupling partners. This work also features a novel strategy for the preparation of macrolactones via intramolecular transesterification of -lactones. The target structure was prepared in 15 steps for the longest linear sequence and 10% overall yield, 24 steps total.