An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5

We report a concise and versatile total synthesis of the diterpenoid (+)‐norcembrene 5 from simple building blocks. Ring‐closing metathesis and an auxiliary‐directed 1,4‐addition are the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structural...

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Detalles Bibliográficos
Autores principales: Breunig, Michael, Yuan, Po, Gaich, Tanja
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/PMC7155007/
https://www.ncbi.nlm.nih.gov/pubmed/31750980
http://dx.doi.org/10.1002/anie.201912613
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author Breunig, Michael
Yuan, Po
Gaich, Tanja
author_facet Breunig, Michael
Yuan, Po
Gaich, Tanja
author_sort Breunig, Michael
collection PubMed
description We report a concise and versatile total synthesis of the diterpenoid (+)‐norcembrene 5 from simple building blocks. Ring‐closing metathesis and an auxiliary‐directed 1,4‐addition are the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structural motif was established from a furanocembranoid through transannular [4+2] cycloaddition.
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spelling pubmed-71550072020-04-15 An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5 Breunig, Michael Yuan, Po Gaich, Tanja Angew Chem Int Ed Engl Communications We report a concise and versatile total synthesis of the diterpenoid (+)‐norcembrene 5 from simple building blocks. Ring‐closing metathesis and an auxiliary‐directed 1,4‐addition are the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structural motif was established from a furanocembranoid through transannular [4+2] cycloaddition. John Wiley and Sons Inc. 2020-02-11 2020-03-27 /pmc/articles/PMC7155007/ /pubmed/31750980 http://dx.doi.org/10.1002/anie.201912613 Text en © 2019 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-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Breunig, Michael
Yuan, Po
Gaich, Tanja
An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5
title An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5
title_full An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5
title_fullStr An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5
title_full_unstemmed An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5
title_short An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)‐Norcembrene 5
title_sort unexpected transannular [4+2] cycloaddition during the total synthesis of (+)‐norcembrene 5
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155007/
https://www.ncbi.nlm.nih.gov/pubmed/31750980
http://dx.doi.org/10.1002/anie.201912613
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