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

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 hig...

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Autores principales: Williams, Simon, Jin, Jialu, Kan, S. B. Jennifer, Li, Mungyuen, Gibson, Lisa J., Paterson, Ian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680201/
https://www.ncbi.nlm.nih.gov/pubmed/27897365
http://dx.doi.org/10.1002/anie.201610636
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author Williams, Simon
Jin, Jialu
Kan, S. B. Jennifer
Li, Mungyuen
Gibson, Lisa J.
Paterson, Ian
author_facet Williams, Simon
Jin, Jialu
Kan, S. B. Jennifer
Li, Mungyuen
Gibson, Lisa J.
Paterson, Ian
author_sort Williams, Simon
collection PubMed
description 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.
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spelling pubmed-66802012019-08-09 An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum Williams, Simon Jin, Jialu Kan, S. B. Jennifer Li, Mungyuen Gibson, Lisa J. Paterson, Ian Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2016-11-29 2017-01-09 /pmc/articles/PMC6680201/ /pubmed/27897365 http://dx.doi.org/10.1002/anie.201610636 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Williams, Simon
Jin, Jialu
Kan, S. B. Jennifer
Li, Mungyuen
Gibson, Lisa J.
Paterson, Ian
An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
title An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
title_full An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
title_fullStr An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
title_full_unstemmed An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
title_short An Expedient Total Synthesis of Chivosazole F: an Actin‐Binding Antimitotic Macrolide from the Myxobacterium Sorangium Cellulosum
title_sort expedient total synthesis of chivosazole f: an actin‐binding antimitotic macrolide from the myxobacterium sorangium cellulosum
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680201/
https://www.ncbi.nlm.nih.gov/pubmed/27897365
http://dx.doi.org/10.1002/anie.201610636
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