An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium  Sorangium Cellulosum | Zendy

Williams Simon | Zendy; Jin Jialu | Zendy; Kan S. B. Jennifer | Zendy; Li Mungyuen | Zendy; Gibson Lisa J. | Zendy; Paterson Ian | Zendy

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

Author(s) -

Williams Simon,

Jin Jialu,

Kan S. B. Jennifer,

Li Mungyuen,

Gibson Lisa J.,

Paterson Ian

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201610636

Subject(s) - total synthesis , chemistry , stereochemistry , stille reaction , myxobacteria , isomerization , combinatorial chemistry , biochemistry , biology , catalysis , genetics , bacteria

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 (2 Z ,4 E ,6 Z ,8 E )‐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.

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