An Expedient Total Synthesis of Chivosazole F: an Actin-Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
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- 作者：Dr. Simon Williams ; Jialu Jin ; Dr. S. B. Jennifer Kan ; Dr. Mungyuen Li ; Dr. Lisa J. Gibson and Prof. Dr. Ian Paterson
- 刊名：Angewandte Chemie International Edition
- 出版年：2017
- 出版时间：January 9, 2017
- 年：2017
- 卷：56
- 期：2
- 页码：645-649
- 全文大小：712K
- ISSN：1521-3773
文摘
A unified strategy for the chemical synthesis of the chivosazoles is described. This strategy is based on two closely related approaches involving the late-stage installation of the isomerization-prone (2Z,4E,6Z,8E)-tetraenoate motif, and an expedient fragment-assembly procedure. The result is a highly convergent total synthesis of chivosazole F through the orchestration of three mild Pd/Cu-mediated Stille cross-coupling reactions, including the use of a one-pot, site-selective, three-component process, in combination with controlled installation of the requisite alkene geometry.