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An Expedient Total Synthesis of Chivosazole?F: an Actin-Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum.

ABSTRACT: 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.

SUBMITTER: Williams S 

PROVIDER: S-EPMC6680201 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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An Expedient Total Synthesis of Chivosazole F: an Actin-Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum.

Williams Simon S   Jin Jialu J   Kan S B Jennifer SB   Li Mungyuen M   Gibson Lisa J LJ   Paterson Ian I  

Angewandte Chemie (International ed. in English) 20161129 2

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  ...[more]

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