Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction

[Image: see text] We designed and executed an expedient synthesis of a complex analogue of the potent immunosuppressive natural product brasilicardin A. Our successful synthesis featured application of our recently developed MHAT-initiated radical bicyclization, which delivered the targeted, complex...

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Autores principales: Niman, Scott W., Buono, Roberta, Fruman, David A., Vanderwal, Christopher D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10204089/
https://www.ncbi.nlm.nih.gov/pubmed/37141632
http://dx.doi.org/10.1021/acs.orglett.3c01019
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author Niman, Scott W.
Buono, Roberta
Fruman, David A.
Vanderwal, Christopher D.
author_facet Niman, Scott W.
Buono, Roberta
Fruman, David A.
Vanderwal, Christopher D.
author_sort Niman, Scott W.
collection PubMed
description [Image: see text] We designed and executed an expedient synthesis of a complex analogue of the potent immunosuppressive natural product brasilicardin A. Our successful synthesis featured application of our recently developed MHAT-initiated radical bicyclization, which delivered the targeted, complex analogue in 17 steps in the longest linear sequence. Unfortunately, this analogue showed no observable immunosuppressive activity, which speaks to the importance of the structural and stereochemical elements of the natural core scaffold.
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spelling pubmed-102040892023-05-24 Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction Niman, Scott W. Buono, Roberta Fruman, David A. Vanderwal, Christopher D. Org Lett [Image: see text] We designed and executed an expedient synthesis of a complex analogue of the potent immunosuppressive natural product brasilicardin A. Our successful synthesis featured application of our recently developed MHAT-initiated radical bicyclization, which delivered the targeted, complex analogue in 17 steps in the longest linear sequence. Unfortunately, this analogue showed no observable immunosuppressive activity, which speaks to the importance of the structural and stereochemical elements of the natural core scaffold. American Chemical Society 2023-05-04 /pmc/articles/PMC10204089/ /pubmed/37141632 http://dx.doi.org/10.1021/acs.orglett.3c01019 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Niman, Scott W.
Buono, Roberta
Fruman, David A.
Vanderwal, Christopher D.
Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction
title Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction
title_full Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction
title_fullStr Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction
title_full_unstemmed Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction
title_short Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction
title_sort synthesis of a complex brasilicardin analogue utilizing a cobalt-catalyzed mhat-induced radical bicyclization reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10204089/
https://www.ncbi.nlm.nih.gov/pubmed/37141632
http://dx.doi.org/10.1021/acs.orglett.3c01019
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AT frumandavida synthesisofacomplexbrasilicardinanalogueutilizingacobaltcatalyzedmhatinducedradicalbicyclizationreaction
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