title: 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.
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Simon
authors.initials: S
authors.lastname: Williams
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Jialu
authors.initials: J
authors.lastname: Jin
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: S B Jennifer
authors.initials: SB
authors.lastname: Kan
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Mungyuen
authors.initials: M
authors.lastname: Li
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Lisa J
authors.initials: LJ
authors.lastname: Gibson
authors.affiliation: University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Ian
authors.initials: I
authors.lastname: Paterson
mesh_terms: D000199:Actins / Q000737:chemistry* / Q000378:metabolism; D050256:Antimitotic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001665:Binding Sites; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009231:Myxococcales / Q000737:chemistry*
chemical_list: D000199:Actins; D050256:Antimitotic Agents; D018942:Macrolides; C547318:chivosazole F
keywords: Stille cross-coupling; macrocycles; macrolides; polyenes; total synthesis