Efforts toward the Total Synthesis of Elisabethin A

[Image: see text] We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a hig...

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Autores principales: Kaiser, Maximilian, Schönbauer, David, Schragl, Katharina, Weil, Matthias, Gaertner, Peter, Enev, Valentin S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680034/
https://www.ncbi.nlm.nih.gov/pubmed/36283031
http://dx.doi.org/10.1021/acs.joc.2c01914
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author Kaiser, Maximilian
Schönbauer, David
Schragl, Katharina
Weil, Matthias
Gaertner, Peter
Enev, Valentin S.
author_facet Kaiser, Maximilian
Schönbauer, David
Schragl, Katharina
Weil, Matthias
Gaertner, Peter
Enev, Valentin S.
author_sort Kaiser, Maximilian
collection PubMed
description [Image: see text] We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an “underdeveloped” Claisen rearrangement of an aryl dienyl ether.
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spelling pubmed-96800342022-11-23 Efforts toward the Total Synthesis of Elisabethin A Kaiser, Maximilian Schönbauer, David Schragl, Katharina Weil, Matthias Gaertner, Peter Enev, Valentin S. J Org Chem [Image: see text] We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an “underdeveloped” Claisen rearrangement of an aryl dienyl ether. American Chemical Society 2022-10-25 2022-11-18 /pmc/articles/PMC9680034/ /pubmed/36283031 http://dx.doi.org/10.1021/acs.joc.2c01914 Text en © 2022 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 Kaiser, Maximilian
Schönbauer, David
Schragl, Katharina
Weil, Matthias
Gaertner, Peter
Enev, Valentin S.
Efforts toward the Total Synthesis of Elisabethin A
title Efforts toward the Total Synthesis of Elisabethin A
title_full Efforts toward the Total Synthesis of Elisabethin A
title_fullStr Efforts toward the Total Synthesis of Elisabethin A
title_full_unstemmed Efforts toward the Total Synthesis of Elisabethin A
title_short Efforts toward the Total Synthesis of Elisabethin A
title_sort efforts toward the total synthesis of elisabethin a
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9680034/
https://www.ncbi.nlm.nih.gov/pubmed/36283031
http://dx.doi.org/10.1021/acs.joc.2c01914
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