A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima

Autores
Bach, Sandra M.; Díaz, Fernando R.; Bach, Horacio; Catalan, Cesar Atilio Nazareno
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Enantiomerically pure (+)-vemolepin was semi-synthesized for the first time using the synthon (6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide [(+)-minimolide], the major sesquiterpene lactone of the Argentinean vine Mikania minima. After performing four consecutive reactions (Cope rearrangement, two oxidations, and selective hydrolysis of the acetate groups) on the synthon (+)-minimolide, a (+)-vernolepin yield of ca. 40% was achieved, proving to be a suitable semi-synthetic strategy for the production of quantities between 0.5-1.0 g of (+)-vernolepin. The transformations described here mimetize the biogenetic pathway for the production of (+)-vernolepin in the genus Vernonia. The synthesized (+)-vernolepin, but not its precursors, shows antifungal activity similar to amphotericin B. The semi-synthesis reported here combines affordable and easily available chemical reagents with classical organic methodologies.
Fil: Bach, Sandra M.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Díaz, Fernando R.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Bach, Horacio. University of British Columbia; Canadá
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Materia
-Vernolepinpin
-Minimolideide
Semi-Synthesis
Antifungal Activity
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/52419
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/52419
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minimaBach, Sandra M.Díaz, Fernando R.Bach, HoracioCatalan, Cesar Atilio Nazareno-Vernolepinpin-MinimolideideSemi-SynthesisAntifungal Activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Enantiomerically pure (+)-vemolepin was semi-synthesized for the first time using the synthon (6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide [(+)-minimolide], the major sesquiterpene lactone of the Argentinean vine Mikania minima. After performing four consecutive reactions (Cope rearrangement, two oxidations, and selective hydrolysis of the acetate groups) on the synthon (+)-minimolide, a (+)-vernolepin yield of ca. 40% was achieved, proving to be a suitable semi-synthetic strategy for the production of quantities between 0.5-1.0 g of (+)-vernolepin. The transformations described here mimetize the biogenetic pathway for the production of (+)-vernolepin in the genus Vernonia. The synthesized (+)-vernolepin, but not its precursors, shows antifungal activity similar to amphotericin B. The semi-synthesis reported here combines affordable and easily available chemical reagents with classical organic methodologies.Fil: Bach, Sandra M.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Díaz, Fernando R.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Bach, Horacio. University of British Columbia; CanadáFil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaNatural Products2011-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52419Bach, Sandra M.; Díaz, Fernando R.; Bach, Horacio; Catalan, Cesar Atilio Nazareno; A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima; Natural Products; Natural Product Communications; 6; 4; 4-2011; 433-4381934-578XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.naturalproduct.us/JournalArchive.aspinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:47:36Zoai:ri.conicet.gov.ar:11336/52419instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:47:36.563CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
title A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
spellingShingle A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
Bach, Sandra M.
-Vernolepinpin
-Minimolideide
Semi-Synthesis
Antifungal Activity
title_short A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
title_full A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
title_fullStr A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
title_full_unstemmed A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
title_sort A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima
dc.creator.none.fl_str_mv Bach, Sandra M.
Díaz, Fernando R.
Bach, Horacio
Catalan, Cesar Atilio Nazareno
author Bach, Sandra M.
author_facet Bach, Sandra M.
Díaz, Fernando R.
Bach, Horacio
Catalan, Cesar Atilio Nazareno
author_role author
author2 Díaz, Fernando R.
Bach, Horacio
Catalan, Cesar Atilio Nazareno
author2_role author
author
author
dc.subject.none.fl_str_mv -Vernolepinpin
-Minimolideide
Semi-Synthesis
Antifungal Activity
topic -Vernolepinpin
-Minimolideide
Semi-Synthesis
Antifungal Activity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Enantiomerically pure (+)-vemolepin was semi-synthesized for the first time using the synthon (6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide [(+)-minimolide], the major sesquiterpene lactone of the Argentinean vine Mikania minima. After performing four consecutive reactions (Cope rearrangement, two oxidations, and selective hydrolysis of the acetate groups) on the synthon (+)-minimolide, a (+)-vernolepin yield of ca. 40% was achieved, proving to be a suitable semi-synthetic strategy for the production of quantities between 0.5-1.0 g of (+)-vernolepin. The transformations described here mimetize the biogenetic pathway for the production of (+)-vernolepin in the genus Vernonia. The synthesized (+)-vernolepin, but not its precursors, shows antifungal activity similar to amphotericin B. The semi-synthesis reported here combines affordable and easily available chemical reagents with classical organic methodologies.
Fil: Bach, Sandra M.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Díaz, Fernando R.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Bach, Horacio. University of British Columbia; Canadá
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
description Enantiomerically pure (+)-vemolepin was semi-synthesized for the first time using the synthon (6S,7R,8S)-8,14-diacetoxy-15-hydroxygermacra-1(10),4,11(13)-trien-6, 12-olide [(+)-minimolide], the major sesquiterpene lactone of the Argentinean vine Mikania minima. After performing four consecutive reactions (Cope rearrangement, two oxidations, and selective hydrolysis of the acetate groups) on the synthon (+)-minimolide, a (+)-vernolepin yield of ca. 40% was achieved, proving to be a suitable semi-synthetic strategy for the production of quantities between 0.5-1.0 g of (+)-vernolepin. The transformations described here mimetize the biogenetic pathway for the production of (+)-vernolepin in the genus Vernonia. The synthesized (+)-vernolepin, but not its precursors, shows antifungal activity similar to amphotericin B. The semi-synthesis reported here combines affordable and easily available chemical reagents with classical organic methodologies.
publishDate 2011
dc.date.none.fl_str_mv 2011-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/52419
Bach, Sandra M.; Díaz, Fernando R.; Bach, Horacio; Catalan, Cesar Atilio Nazareno; A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima; Natural Products; Natural Product Communications; 6; 4; 4-2011; 433-438
1934-578X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52419
identifier_str_mv Bach, Sandra M.; Díaz, Fernando R.; Bach, Horacio; Catalan, Cesar Atilio Nazareno; A facile and efficient four-step enantioselective synthesis of (+)-vernolepin from (+)-minimolide, the major germacranolide of Mikania minima; Natural Products; Natural Product Communications; 6; 4; 4-2011; 433-438
1934-578X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.naturalproduct.us/JournalArchive.asp
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Natural Products
publisher.none.fl_str_mv Natural Products
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844614520550457344
score 13.070432

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