Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route

[Image: see text] The evolution of an enantioselective total synthesis of (+)-18-epi-latrunculol A, a congener of the marine-sponge-derived latrunculins A and B, is reported. Key steps include a late-stage Mitsunobu macrolactonization to construct the 16-membered macrolactone, a mild Carreira alkyny...

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Detalles Bibliográficos
Autores principales: Williams, Brett D., Smith, Amos B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184459/
https://www.ncbi.nlm.nih.gov/pubmed/25243951
http://dx.doi.org/10.1021/jo501733m
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author Williams, Brett D.
Smith, Amos B.
author_facet Williams, Brett D.
Smith, Amos B.
author_sort Williams, Brett D.
collection PubMed
description [Image: see text] The evolution of an enantioselective total synthesis of (+)-18-epi-latrunculol A, a congener of the marine-sponge-derived latrunculins A and B, is reported. Key steps include a late-stage Mitsunobu macrolactonization to construct the 16-membered macrolactone, a mild Carreira alkynylation to unite the northern and southern hemispheres, a diastereoselective, acid-mediated δ-hydroxy enone cyclization/equilibration sequence, and a functional-group-tolerant cross-metathesis to access the enone cyclization precursor.
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spelling pubmed-41844592015-09-22 Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route Williams, Brett D. Smith, Amos B. J Org Chem [Image: see text] The evolution of an enantioselective total synthesis of (+)-18-epi-latrunculol A, a congener of the marine-sponge-derived latrunculins A and B, is reported. Key steps include a late-stage Mitsunobu macrolactonization to construct the 16-membered macrolactone, a mild Carreira alkynylation to unite the northern and southern hemispheres, a diastereoselective, acid-mediated δ-hydroxy enone cyclization/equilibration sequence, and a functional-group-tolerant cross-metathesis to access the enone cyclization precursor. American Chemical Society 2014-09-22 2014-10-03 /pmc/articles/PMC4184459/ /pubmed/25243951 http://dx.doi.org/10.1021/jo501733m Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Williams, Brett D.
Smith, Amos B.
Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route
title Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route
title_full Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route
title_fullStr Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route
title_full_unstemmed Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route
title_short Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route
title_sort total synthesis of (+)-18-epi-latrunculol a: development of a synthetic route
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184459/
https://www.ncbi.nlm.nih.gov/pubmed/25243951
http://dx.doi.org/10.1021/jo501733m
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