Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids

[Image: see text] The development of the first enantioselective para-Claisen rearrangement has been achieved. Using a chiral aluminum Lewis acid, illicinole is rearranged to give (−)-illicinone A (er 87:13), which can then be converted into more complex Illicium-derived prenylated phenylpropanoids....

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Autores principales: Homer, Joshua A., De Silvestro, Irene, Matheson, Eilidh J., Stuart, Jake T., Lawrence, Andrew L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155563/
https://www.ncbi.nlm.nih.gov/pubmed/33856817
http://dx.doi.org/10.1021/acs.orglett.1c00620
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author Homer, Joshua A.
De Silvestro, Irene
Matheson, Eilidh J.
Stuart, Jake T.
Lawrence, Andrew L.
author_facet Homer, Joshua A.
De Silvestro, Irene
Matheson, Eilidh J.
Stuart, Jake T.
Lawrence, Andrew L.
author_sort Homer, Joshua A.
collection PubMed
description [Image: see text] The development of the first enantioselective para-Claisen rearrangement has been achieved. Using a chiral aluminum Lewis acid, illicinole is rearranged to give (−)-illicinone A (er 87:13), which can then be converted into more complex Illicium-derived prenylated phenylpropanoids. The absolute configurations of the natural products (+)-cycloillicinone and (−)-illicarborene A have been determined, and our results cast doubt on the enantiopurity of the natural samples.
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spelling pubmed-81555632021-05-28 Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids Homer, Joshua A. De Silvestro, Irene Matheson, Eilidh J. Stuart, Jake T. Lawrence, Andrew L. Org Lett [Image: see text] The development of the first enantioselective para-Claisen rearrangement has been achieved. Using a chiral aluminum Lewis acid, illicinole is rearranged to give (−)-illicinone A (er 87:13), which can then be converted into more complex Illicium-derived prenylated phenylpropanoids. The absolute configurations of the natural products (+)-cycloillicinone and (−)-illicarborene A have been determined, and our results cast doubt on the enantiopurity of the natural samples. American Chemical Society 2021-04-15 2021-05-07 /pmc/articles/PMC8155563/ /pubmed/33856817 http://dx.doi.org/10.1021/acs.orglett.1c00620 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Homer, Joshua A.
De Silvestro, Irene
Matheson, Eilidh J.
Stuart, Jake T.
Lawrence, Andrew L.
Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids
title Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids
title_full Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids
title_fullStr Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids
title_full_unstemmed Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids
title_short Enantioselective para-Claisen Rearrangement for the Synthesis of Illicium-Derived Prenylated Phenylpropanoids
title_sort enantioselective para-claisen rearrangement for the synthesis of illicium-derived prenylated phenylpropanoids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155563/
https://www.ncbi.nlm.nih.gov/pubmed/33856817
http://dx.doi.org/10.1021/acs.orglett.1c00620
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