Enantioselective total synthesis of (−)-myrifabral A and B

A catalytic enantioselective approach to the Myrioneuron alkaloids (−)-myrifabral A and (−)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization f...

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Detalles Bibliográficos
Autores principales: Fulton, Tyler J., Chen, Anthony Y., Bartberger, Michael D., Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162428/
https://www.ncbi.nlm.nih.gov/pubmed/34094334
http://dx.doi.org/10.1039/d0sc01141j
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author Fulton, Tyler J.
Chen, Anthony Y.
Bartberger, Michael D.
Stoltz, Brian M.
author_facet Fulton, Tyler J.
Chen, Anthony Y.
Bartberger, Michael D.
Stoltz, Brian M.
author_sort Fulton, Tyler J.
collection PubMed
description A catalytic enantioselective approach to the Myrioneuron alkaloids (−)-myrifabral A and (−)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (−)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (−)-myrifabral A to (−)-myrifabral B.
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spelling pubmed-81624282021-06-04 Enantioselective total synthesis of (−)-myrifabral A and B Fulton, Tyler J. Chen, Anthony Y. Bartberger, Michael D. Stoltz, Brian M. Chem Sci Chemistry A catalytic enantioselective approach to the Myrioneuron alkaloids (−)-myrifabral A and (−)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (−)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (−)-myrifabral A to (−)-myrifabral B. The Royal Society of Chemistry 2020-04-21 /pmc/articles/PMC8162428/ /pubmed/34094334 http://dx.doi.org/10.1039/d0sc01141j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Fulton, Tyler J.
Chen, Anthony Y.
Bartberger, Michael D.
Stoltz, Brian M.
Enantioselective total synthesis of (−)-myrifabral A and B
title Enantioselective total synthesis of (−)-myrifabral A and B
title_full Enantioselective total synthesis of (−)-myrifabral A and B
title_fullStr Enantioselective total synthesis of (−)-myrifabral A and B
title_full_unstemmed Enantioselective total synthesis of (−)-myrifabral A and B
title_short Enantioselective total synthesis of (−)-myrifabral A and B
title_sort enantioselective total synthesis of (−)-myrifabral a and b
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162428/
https://www.ncbi.nlm.nih.gov/pubmed/34094334
http://dx.doi.org/10.1039/d0sc01141j
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