Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor

Detalhes bibliográficos
Autor(a) principal: Guerrero, Palimecio G.
Data de Publicação: 2012
Outros Autores: Oliveira, Paulo R. de, Baroni, Adriano C. M., Marques, Francisco A., Labes, Ricardo, Hurtado, Gabriela R., Dabdoub, Miguel J. [UNESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1016/j.tetlet.2012.07.092
http://hdl.handle.net/11449/194747
Resumo: An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.
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spelling Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursorRetinoidTemaroteneArotinoid acid (TTNPB)Synthesis(Z)-1,2-bis(organylchalcogene)-1-alkeneAnticancerAn efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundacao AraucariaParana Fed Univ Technol, UTFPR, DAQBi, Dept Chem & Biol, Curitiba, Parana, BrazilUniv Fed Mato Grosso do Sul, UFMS, Dept Pharm Biochem, Campo Grande, MS, BrazilUniv Fed Parana, UFPR, Dept Chem, BR-80060000 Curitiba, Parana, BrazilUniv Fed Mato Grosso do Sul, UFMS, Dept Chem, Campo Grande, MS, BrazilSao Paulo State Univ, USP, Dept Chem, Ribeirao Preto, SP, BrazilSao Paulo State Univ, USP, Dept Chem, Ribeirao Preto, SP, BrazilElsevier B.V.Parana Fed Univ TechnolUniversidade Federal de Mato Grosso do Sul (UFMS)Universidade Federal do Paraná (UFPR)Universidade Estadual Paulista (Unesp)Guerrero, Palimecio G.Oliveira, Paulo R. deBaroni, Adriano C. M.Marques, Francisco A.Labes, RicardoHurtado, Gabriela R.Dabdoub, Miguel J. [UNESP]2020-12-10T16:36:24Z2020-12-10T16:36:24Z2012-09-26info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article5302-5305http://dx.doi.org/10.1016/j.tetlet.2012.07.092Tetrahedron Letters. Oxford: Pergamon-elsevier Science Ltd, v. 53, n. 39, p. 5302-5305, 2012.0040-4039http://hdl.handle.net/11449/19474710.1016/j.tetlet.2012.07.092WOS:000308628900027Web of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengTetrahedron Lettersinfo:eu-repo/semantics/openAccess2021-10-22T20:28:48Zoai:repositorio.unesp.br:11449/194747Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T22:44:14.407860Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
title Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
spellingShingle Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
Guerrero, Palimecio G.
Retinoid
Temarotene
Arotinoid acid (TTNPB)
Synthesis
(Z)-1,2-bis(organylchalcogene)-1-alkene
Anticancer
title_short Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
title_full Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
title_fullStr Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
title_full_unstemmed Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
title_sort Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
author Guerrero, Palimecio G.
author_facet Guerrero, Palimecio G.
Oliveira, Paulo R. de
Baroni, Adriano C. M.
Marques, Francisco A.
Labes, Ricardo
Hurtado, Gabriela R.
Dabdoub, Miguel J. [UNESP]
author_role author
author2 Oliveira, Paulo R. de
Baroni, Adriano C. M.
Marques, Francisco A.
Labes, Ricardo
Hurtado, Gabriela R.
Dabdoub, Miguel J. [UNESP]
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Parana Fed Univ Technol
Universidade Federal de Mato Grosso do Sul (UFMS)
Universidade Federal do Paraná (UFPR)
Universidade Estadual Paulista (Unesp)
dc.contributor.author.fl_str_mv Guerrero, Palimecio G.
Oliveira, Paulo R. de
Baroni, Adriano C. M.
Marques, Francisco A.
Labes, Ricardo
Hurtado, Gabriela R.
Dabdoub, Miguel J. [UNESP]
dc.subject.por.fl_str_mv Retinoid
Temarotene
Arotinoid acid (TTNPB)
Synthesis
(Z)-1,2-bis(organylchalcogene)-1-alkene
Anticancer
topic Retinoid
Temarotene
Arotinoid acid (TTNPB)
Synthesis
(Z)-1,2-bis(organylchalcogene)-1-alkene
Anticancer
description An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the beta-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. (c) 2012 Elsevier Ltd. All rights reserved.
publishDate 2012
dc.date.none.fl_str_mv 2012-09-26
2020-12-10T16:36:24Z
2020-12-10T16:36:24Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://dx.doi.org/10.1016/j.tetlet.2012.07.092
Tetrahedron Letters. Oxford: Pergamon-elsevier Science Ltd, v. 53, n. 39, p. 5302-5305, 2012.
0040-4039
http://hdl.handle.net/11449/194747
10.1016/j.tetlet.2012.07.092
WOS:000308628900027
url http://dx.doi.org/10.1016/j.tetlet.2012.07.092
http://hdl.handle.net/11449/194747
identifier_str_mv Tetrahedron Letters. Oxford: Pergamon-elsevier Science Ltd, v. 53, n. 39, p. 5302-5305, 2012.
0040-4039
10.1016/j.tetlet.2012.07.092
WOS:000308628900027
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Tetrahedron Letters
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 5302-5305
dc.publisher.none.fl_str_mv Elsevier B.V.
publisher.none.fl_str_mv Elsevier B.V.
dc.source.none.fl_str_mv Web of Science
reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv
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