Synthesis of arotinoid acid and temarotene using mixed (Z)-1,2-bis(organylchalcogene)-1-alkene as precursor
Autor(a) principal: | |
---|---|
Data de Publicação: | 2012 |
Outros Autores: | , , , , , |
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. |
id |
UNSP_d996622ad22f78385c66e19178fefbb4 |
---|---|
oai_identifier_str |
oai:repositorio.unesp.br:11449/194747 |
network_acronym_str |
UNSP |
network_name_str |
Repositório Institucional da UNESP |
repository_id_str |
2946 |
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 |
|
_version_ |
1808129456251863040 |