Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction

[Image: see text] The stereoselective synthesis of C(40)-all-trans-carotenoids with the formal hexahydrobenzofuran skeletons aurochrome, auroxanthin, and equinenone-5′,8′-epoxide is reported. The synthesis is based on a one-pot or stepwise double Horner–Wadsworth–Emmons (HWE) reaction of a terminal...

Descripción completa

Detalles Bibliográficos
Autores principales: Rivas, Aurea, Castiñeira, Marta, Álvarez, Rosana, Vaz, Belén, de Lera, Angel R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9693700/
https://www.ncbi.nlm.nih.gov/pubmed/36121920
http://dx.doi.org/10.1021/acs.jnatprod.2c00475
_version_ 1784837609263988736
author Rivas, Aurea
Castiñeira, Marta
Álvarez, Rosana
Vaz, Belén
de Lera, Angel R.
author_facet Rivas, Aurea
Castiñeira, Marta
Álvarez, Rosana
Vaz, Belén
de Lera, Angel R.
author_sort Rivas, Aurea
collection PubMed
description [Image: see text] The stereoselective synthesis of C(40)-all-trans-carotenoids with the formal hexahydrobenzofuran skeletons aurochrome, auroxanthin, and equinenone-5′,8′-epoxide is reported. The synthesis is based on a one-pot or stepwise double Horner–Wadsworth–Emmons (HWE) reaction of a terminal enantiopure C(15)-5,6-epoxycyclohexadienylphosphonate and a central C(10)-trienedial. The ring expansion of the epoxycyclohexadienylphosphonate, generated by a Stille cross-coupling reaction, to the hexahydrobenzofuran skeleton was promoted by the reaction conditions of the HWE reaction prior to double-bond formation.
format Online
Article
Text
id pubmed-9693700
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society and American Society of Pharmacognosy
record_format MEDLINE/PubMed
spelling pubmed-96937002022-11-26 Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction Rivas, Aurea Castiñeira, Marta Álvarez, Rosana Vaz, Belén de Lera, Angel R. J Nat Prod [Image: see text] The stereoselective synthesis of C(40)-all-trans-carotenoids with the formal hexahydrobenzofuran skeletons aurochrome, auroxanthin, and equinenone-5′,8′-epoxide is reported. The synthesis is based on a one-pot or stepwise double Horner–Wadsworth–Emmons (HWE) reaction of a terminal enantiopure C(15)-5,6-epoxycyclohexadienylphosphonate and a central C(10)-trienedial. The ring expansion of the epoxycyclohexadienylphosphonate, generated by a Stille cross-coupling reaction, to the hexahydrobenzofuran skeleton was promoted by the reaction conditions of the HWE reaction prior to double-bond formation. American Chemical Society and American Society of Pharmacognosy 2022-09-19 2022-10-28 /pmc/articles/PMC9693700/ /pubmed/36121920 http://dx.doi.org/10.1021/acs.jnatprod.2c00475 Text en © 2022 American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Rivas, Aurea
Castiñeira, Marta
Álvarez, Rosana
Vaz, Belén
de Lera, Angel R.
Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
title Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
title_full Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
title_fullStr Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
title_full_unstemmed Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
title_short Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
title_sort stereoselective synthesis of bisfuranoxide (aurochrome, auroxanthin) and monofuranoxide (equinenone 5′,8′-epoxide) carotenoids by double horner–wadsworth–emmons reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9693700/
https://www.ncbi.nlm.nih.gov/pubmed/36121920
http://dx.doi.org/10.1021/acs.jnatprod.2c00475
work_keys_str_mv AT rivasaurea stereoselectivesynthesisofbisfuranoxideaurochromeauroxanthinandmonofuranoxideequinenone58epoxidecarotenoidsbydoublehornerwadsworthemmonsreaction
AT castineiramarta stereoselectivesynthesisofbisfuranoxideaurochromeauroxanthinandmonofuranoxideequinenone58epoxidecarotenoidsbydoublehornerwadsworthemmonsreaction
AT alvarezrosana stereoselectivesynthesisofbisfuranoxideaurochromeauroxanthinandmonofuranoxideequinenone58epoxidecarotenoidsbydoublehornerwadsworthemmonsreaction
AT vazbelen stereoselectivesynthesisofbisfuranoxideaurochromeauroxanthinandmonofuranoxideequinenone58epoxidecarotenoidsbydoublehornerwadsworthemmonsreaction
AT deleraangelr stereoselectivesynthesisofbisfuranoxideaurochromeauroxanthinandmonofuranoxideequinenone58epoxidecarotenoidsbydoublehornerwadsworthemmonsreaction

Ejemplares similares