Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin

[Image: see text] The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins–Peterson cyclization in their core construction. In only one step, a seven-member...

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Autores principales: Sinka, Victoria, Cruz, Daniel A., Martín, Víctor S., Padrón, Juan I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9344465/
https://www.ncbi.nlm.nih.gov/pubmed/35834432
http://dx.doi.org/10.1021/acs.orglett.2c01769
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author Sinka, Victoria
Cruz, Daniel A.
Martín, Víctor S.
Padrón, Juan I.
author_facet Sinka, Victoria
Cruz, Daniel A.
Martín, Víctor S.
Padrón, Juan I.
author_sort Sinka, Victoria
collection PubMed
description [Image: see text] The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins–Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ(4) position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to accede to the bromodioxabicycle on (+)-neoisoprelaurefucin.
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spelling pubmed-93444652022-08-03 Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin Sinka, Victoria Cruz, Daniel A. Martín, Víctor S. Padrón, Juan I. Org Lett [Image: see text] The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin have been accomplished. These syntheses were based on a common parallel synthetic strategy using Prins–Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ(4) position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to accede to the bromodioxabicycle on (+)-neoisoprelaurefucin. American Chemical Society 2022-07-14 2022-07-29 /pmc/articles/PMC9344465/ /pubmed/35834432 http://dx.doi.org/10.1021/acs.orglett.2c01769 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 Sinka, Victoria
Cruz, Daniel A.
Martín, Víctor S.
Padrón, Juan I.
Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin
title Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin
title_full Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin
title_fullStr Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin
title_full_unstemmed Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin
title_short Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin
title_sort shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9344465/
https://www.ncbi.nlm.nih.gov/pubmed/35834432
http://dx.doi.org/10.1021/acs.orglett.2c01769
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