Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core

The hamigeran family of natural products has been the target of numerous synthetic efforts due to its biological activity and interesting structural properties. Herein we disclose our efforts toward the synthesis of hamigerans C and D, unique among the initially isolated members due to their 6-7-5 c...

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Autores principales: Duquette, Douglas C., Jensen, Thomas, Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5788718/
https://www.ncbi.nlm.nih.gov/pubmed/28874851
http://dx.doi.org/10.1038/ja.2017.96
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author Duquette, Douglas C.
Jensen, Thomas
Stoltz, Brian M.
author_facet Duquette, Douglas C.
Jensen, Thomas
Stoltz, Brian M.
author_sort Duquette, Douglas C.
collection PubMed
description The hamigeran family of natural products has been the target of numerous synthetic efforts due to its biological activity and interesting structural properties. Herein we disclose our efforts toward the synthesis of hamigerans C and D, unique among the initially isolated members due to their 6-7-5 carbocyclic core. Our approach directly targets this tricyclic motif by sequential Negishi and Heck coupling reactions, yielding an advanced intermediate with all necessary carbons and sufficient functionality poised for completion of the synthesis of these two natural products.
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spelling pubmed-57887182018-03-06 Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core Duquette, Douglas C. Jensen, Thomas Stoltz, Brian M. J Antibiot (Tokyo) Article The hamigeran family of natural products has been the target of numerous synthetic efforts due to its biological activity and interesting structural properties. Herein we disclose our efforts toward the synthesis of hamigerans C and D, unique among the initially isolated members due to their 6-7-5 carbocyclic core. Our approach directly targets this tricyclic motif by sequential Negishi and Heck coupling reactions, yielding an advanced intermediate with all necessary carbons and sufficient functionality poised for completion of the synthesis of these two natural products. 2017-09-06 2018-02 /pmc/articles/PMC5788718/ /pubmed/28874851 http://dx.doi.org/10.1038/ja.2017.96 Text en Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use: http://www.nature.com/authors/editorial_policies/license.html#terms
spellingShingle Article
Duquette, Douglas C.
Jensen, Thomas
Stoltz, Brian M.
Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core
title Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core
title_full Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core
title_fullStr Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core
title_full_unstemmed Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core
title_short Progress Toward the Total Synthesis of Hamigerans C and D: A Direct Approach to an Elaborated 6-7-5 Carbocyclic Core
title_sort progress toward the total synthesis of hamigerans c and d: a direct approach to an elaborated 6-7-5 carbocyclic core
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5788718/
https://www.ncbi.nlm.nih.gov/pubmed/28874851
http://dx.doi.org/10.1038/ja.2017.96
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