Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits

Detalhes bibliográficos
Autor(a) principal: Sartori, Suélen Karine
Data de Publicação: 2021
Outros Autores: Miranda, Izabel L., Matos, Davi A. de, Kohlhoff, Markus, Diaz, Marisa A. N., Diaz-Muñoz, Gaspar
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/51142
Resumo: Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil
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spelling Sartori, Suélen KarineMiranda, Izabel L.Matos, Davi A. deKohlhoff, MarkusDiaz, Marisa A. N.Diaz-Muñoz, Gaspar2022-02-10T18:11:58Z2022-02-10T18:11:58Z2021SARTORI, Suélen Karine et al. Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits. J. Braz. Chem. Soc., v. 32, n. 4, p. 757- 766, 2021 • https://doi.org/10.21577/0103-5053.202002270103-5053https://www.arca.fiocruz.br/handle/icict/51142engSociedade Brasileira de QuímicaSynthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunitsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilFundação Oswaldo Cruz. Instituto René Rachou. Química de Produtos Naturais. Belo Horizonte, MG, BrazilUniversidade Federal de Viçosa. Departamento de Bioquímica e Biologia Molecula. Viçosa,MG, BrazilUniversidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, BrazilThis study describes the stereoselective synthesis of two new γ-lactones in 6 and 3 steps and 19 and 32% yield, respectively, directed toward the total synthesis of the natural product (−)-cleistenolide. The starting material was an enantiomerically pure diacetonide diol, derived from d-mannitol with the required stereocenters for (−)-cleistenolide synthesis. γ-Lactone syntheses were based on highly selective protection and deprotection of hydroxyls from d-mannitol. The formation of γ-lactone rings was the culmination of this approach, made possible by a Horner-Wadsworth-Emmons Z-olefination between diacetal aldehyde and ethyl 2-(bis(o-tolyloxy)phosphoryl)acetate to produce an unsaturated ester. The Z-isomer ester was highly favored in relation to the E-isomer (Z/E ratio of 94:6), allowing the formation of the γ-lactone ring under acid catalysis. This strategy precluded the use of chiral auxiliaries or catalysts for the control of stereocenters in the novel γ-lactones(−)-cleistenolideγ-lactonediacetonide diold-mannitolinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-83082https://www.arca.fiocruz.br/bitstream/icict/51142/1/license.txt9193a7c197bc67acd023525e72a03240MD51ORIGINALSynthetic Studies toward (-)-Cleistenolide.pdfSynthetic Studies toward (-)-Cleistenolide.pdfapplication/pdf3671457https://www.arca.fiocruz.br/bitstream/icict/51142/2/Synthetic%20Studies%20toward%20%28-%29-Cleistenolide.pdf7bf368540f73b46bf405d863e7243c90MD52icict/511422022-02-10 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dc.title.pt_BR.fl_str_mv Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
title Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
spellingShingle Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
Sartori, Suélen Karine
(−)-cleistenolide
γ-lactone
diacetonide diol
d-mannitol
title_short Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
title_full Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
title_fullStr Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
title_full_unstemmed Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
title_sort Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits
author Sartori, Suélen Karine
author_facet Sartori, Suélen Karine
Miranda, Izabel L.
Matos, Davi A. de
Kohlhoff, Markus
Diaz, Marisa A. N.
Diaz-Muñoz, Gaspar
author_role author
author2 Miranda, Izabel L.
Matos, Davi A. de
Kohlhoff, Markus
Diaz, Marisa A. N.
Diaz-Muñoz, Gaspar
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Sartori, Suélen Karine
Miranda, Izabel L.
Matos, Davi A. de
Kohlhoff, Markus
Diaz, Marisa A. N.
Diaz-Muñoz, Gaspar
dc.subject.en.pt_BR.fl_str_mv (−)-cleistenolide
γ-lactone
diacetonide diol
d-mannitol
topic (−)-cleistenolide
γ-lactone
diacetonide diol
d-mannitol
description Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil
publishDate 2021
dc.date.issued.fl_str_mv 2021
dc.date.accessioned.fl_str_mv 2022-02-10T18:11:58Z
dc.date.available.fl_str_mv 2022-02-10T18:11:58Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.citation.fl_str_mv SARTORI, Suélen Karine et al. Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits. J. Braz. Chem. Soc., v. 32, n. 4, p. 757- 766, 2021 • https://doi.org/10.21577/0103-5053.20200227
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/51142
dc.identifier.issn.pt_BR.fl_str_mv 0103-5053
identifier_str_mv SARTORI, Suélen Karine et al. Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits. J. Braz. Chem. Soc., v. 32, n. 4, p. 757- 766, 2021 • https://doi.org/10.21577/0103-5053.20200227
0103-5053
url https://www.arca.fiocruz.br/handle/icict/51142
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
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collection Repositório Institucional da FIOCRUZ (ARCA)
bitstream.url.fl_str_mv https://www.arca.fiocruz.br/bitstream/icict/51142/1/license.txt
https://www.arca.fiocruz.br/bitstream/icict/51142/2/Synthetic%20Studies%20toward%20%28-%29-Cleistenolide.pdf
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repository.name.fl_str_mv Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)
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