A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF(6)], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic c...

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Autores principales: Kanojia, Seema V, Chatterjee, Sucheta, Chattopadhyay, Subrata, Goswami, Dibakar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6404422/
https://www.ncbi.nlm.nih.gov/pubmed/30873232
http://dx.doi.org/10.3762/bjoc.15.42
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author Kanojia, Seema V
Chatterjee, Sucheta
Chattopadhyay, Subrata
Goswami, Dibakar
author_facet Kanojia, Seema V
Chatterjee, Sucheta
Chattopadhyay, Subrata
Goswami, Dibakar
author_sort Kanojia, Seema V
collection PubMed
description A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF(6)], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic centers. The further conversion to the appropriate intermediates and subsequent acylation with lauric acid furnished the target compound.
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spelling pubmed-64044222019-03-14 A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12 Kanojia, Seema V Chatterjee, Sucheta Chattopadhyay, Subrata Goswami, Dibakar Beilstein J Org Chem Full Research Paper A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF(6)], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic centers. The further conversion to the appropriate intermediates and subsequent acylation with lauric acid furnished the target compound. Beilstein-Institut 2019-02-18 /pmc/articles/PMC6404422/ /pubmed/30873232 http://dx.doi.org/10.3762/bjoc.15.42 Text en Copyright © 2019, Kanojia et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Kanojia, Seema V
Chatterjee, Sucheta
Chattopadhyay, Subrata
Goswami, Dibakar
A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
title A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
title_full A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
title_fullStr A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
title_full_unstemmed A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
title_short A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12
title_sort chemoenzymatic synthesis of ceramide trafficking inhibitor hpa-12
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6404422/
https://www.ncbi.nlm.nih.gov/pubmed/30873232
http://dx.doi.org/10.3762/bjoc.15.42
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