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Asymmetric synthesis of a stereopentade fragment toward latrunculins

Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in the literature all target simi...

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Autores principales: Joyeux, Benjamin, Gamet, Antoine, Casaretto, Nicolas, Nay, Bastien
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10113517/
https://www.ncbi.nlm.nih.gov/pubmed/37091733
http://dx.doi.org/10.3762/bjoc.19.32
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author Joyeux, Benjamin
Gamet, Antoine
Casaretto, Nicolas
Nay, Bastien
author_facet Joyeux, Benjamin
Gamet, Antoine
Casaretto, Nicolas
Nay, Bastien
author_sort Joyeux, Benjamin
collection PubMed
description Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in the literature all target similar disconnections, especially an aldol strategy involving a recurrent 4-acetyl-1,3-thiazolidin-2-one ketone partner. Herein, we describe an alternative disconnection and subsequent stereoselective transformations to construct a stereopentade amenable to latrunculin and analogue synthesis, starting from (+)-β-citronellene. Key stereoselective transformations involve an asymmetric Krische allylation, an aldol reaction under 1,5-anti stereocontrol, and a Tishchenko–Evans reduction accompanied by a peculiar ester transposition, allowing to install key stereogenic centers of the natural products.
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spelling pubmed-101135172023-04-20 Asymmetric synthesis of a stereopentade fragment toward latrunculins Joyeux, Benjamin Gamet, Antoine Casaretto, Nicolas Nay, Bastien Beilstein J Org Chem Letter Latrunculins are marine toxins used in cell biology to block actin polymerization. The development of new synthetic strategies and methods for their synthesis is thus important in order to improve, modulate or control this biological value. The total syntheses found in the literature all target similar disconnections, especially an aldol strategy involving a recurrent 4-acetyl-1,3-thiazolidin-2-one ketone partner. Herein, we describe an alternative disconnection and subsequent stereoselective transformations to construct a stereopentade amenable to latrunculin and analogue synthesis, starting from (+)-β-citronellene. Key stereoselective transformations involve an asymmetric Krische allylation, an aldol reaction under 1,5-anti stereocontrol, and a Tishchenko–Evans reduction accompanied by a peculiar ester transposition, allowing to install key stereogenic centers of the natural products. Beilstein-Institut 2023-04-03 /pmc/articles/PMC10113517/ /pubmed/37091733 http://dx.doi.org/10.3762/bjoc.19.32 Text en Copyright © 2023, Joyeux et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Joyeux, Benjamin
Gamet, Antoine
Casaretto, Nicolas
Nay, Bastien
Asymmetric synthesis of a stereopentade fragment toward latrunculins
title Asymmetric synthesis of a stereopentade fragment toward latrunculins
title_full Asymmetric synthesis of a stereopentade fragment toward latrunculins
title_fullStr Asymmetric synthesis of a stereopentade fragment toward latrunculins
title_full_unstemmed Asymmetric synthesis of a stereopentade fragment toward latrunculins
title_short Asymmetric synthesis of a stereopentade fragment toward latrunculins
title_sort asymmetric synthesis of a stereopentade fragment toward latrunculins
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10113517/
https://www.ncbi.nlm.nih.gov/pubmed/37091733
http://dx.doi.org/10.3762/bjoc.19.32
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