Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX

The cross‐conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael‐type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of...

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Detalles Bibliográficos
Autores principales: Huang, Jing‐Kai, Shia, Kak‐Shan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187479/
https://www.ncbi.nlm.nih.gov/pubmed/31944523
http://dx.doi.org/10.1002/anie.201914657
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author Huang, Jing‐Kai
Shia, Kak‐Shan
author_facet Huang, Jing‐Kai
Shia, Kak‐Shan
author_sort Huang, Jing‐Kai
collection PubMed
description The cross‐conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael‐type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully achieved in a concise 7‐step sequence with an overall yield of about 20 %.
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spelling pubmed-71874792020-04-29 Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX Huang, Jing‐Kai Shia, Kak‐Shan Angew Chem Int Ed Engl Communications The cross‐conjugated vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael‐type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully achieved in a concise 7‐step sequence with an overall yield of about 20 %. John Wiley and Sons Inc. 2020-02-25 2020-04-16 /pmc/articles/PMC7187479/ /pubmed/31944523 http://dx.doi.org/10.1002/anie.201914657 Text en © 2020 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
Huang, Jing‐Kai
Shia, Kak‐Shan
Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
title Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
title_full Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
title_fullStr Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
title_full_unstemmed Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
title_short Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
title_sort development of a cross‐conjugated vinylogous [4+2] anionic annulation and application to the total synthesis of natural antibiotic (±)‐abx
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187479/
https://www.ncbi.nlm.nih.gov/pubmed/31944523
http://dx.doi.org/10.1002/anie.201914657
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