Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement

In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly stereoselective sequence involving a Myers alkylation and a Shi epoxidation. Ring-opening of this epoxide with a vinylcopper complex afforded alcohol 26 instead of the expected produc...

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Autores principales: Loertscher, Brad M, Zhang, Yu, Castle, Steven L
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701374/
https://www.ncbi.nlm.nih.gov/pubmed/23843911
http://dx.doi.org/10.3762/bjoc.9.132
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author Loertscher, Brad M
Zhang, Yu
Castle, Steven L
author_facet Loertscher, Brad M
Zhang, Yu
Castle, Steven L
author_sort Loertscher, Brad M
collection PubMed
description In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly stereoselective sequence involving a Myers alkylation and a Shi epoxidation. Ring-opening of this epoxide with a vinylcopper complex afforded alcohol 26 instead of the expected product 27. An unusual Lewis acid promoted Payne rearrangement of an α-trityloxy epoxide is proposed to account for this outcome.
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spelling pubmed-37013742013-07-10 Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement Loertscher, Brad M Zhang, Yu Castle, Steven L Beilstein J Org Chem Full Research Paper In the context of synthetic efforts targeting the alkaloid lyconadin A, scalemic epoxide 25 was prepared by a highly stereoselective sequence involving a Myers alkylation and a Shi epoxidation. Ring-opening of this epoxide with a vinylcopper complex afforded alcohol 26 instead of the expected product 27. An unusual Lewis acid promoted Payne rearrangement of an α-trityloxy epoxide is proposed to account for this outcome. Beilstein-Institut 2013-06-18 /pmc/articles/PMC3701374/ /pubmed/23843911 http://dx.doi.org/10.3762/bjoc.9.132 Text en Copyright © 2013, Loertscher et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Loertscher, Brad M
Zhang, Yu
Castle, Steven L
Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement
title Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement
title_full Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement
title_fullStr Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement
title_full_unstemmed Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement
title_short Exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin A and discovery of an unexpected Payne rearrangement
title_sort exploration of an epoxidation–ring-opening strategy for the synthesis of lyconadin a and discovery of an unexpected payne rearrangement
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701374/
https://www.ncbi.nlm.nih.gov/pubmed/23843911
http://dx.doi.org/10.3762/bjoc.9.132
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