Total Synthesis of Loroxanthin

The first total synthesis of loroxanthin (1) was accomplished by Horner-Wadsworth-Emmons reaction of C(25)-apocarotenal 8 having a silyl-protected 19-hydroxy moiety with C(15)-phosphonate 25 bearing a silyl-protected 3-hydroxy-ε-end group. Preparation of apocarotenal 8 was achieved via Stille coupli...

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Autores principales: Yamano, Yumiko, Tanabe, Mari, Shimada, Atsushi, Wada, Akimori
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9699617/
https://www.ncbi.nlm.nih.gov/pubmed/36354981
http://dx.doi.org/10.3390/md20110658
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author Yamano, Yumiko
Tanabe, Mari
Shimada, Atsushi
Wada, Akimori
author_facet Yamano, Yumiko
Tanabe, Mari
Shimada, Atsushi
Wada, Akimori
author_sort Yamano, Yumiko
collection PubMed
description The first total synthesis of loroxanthin (1) was accomplished by Horner-Wadsworth-Emmons reaction of C(25)-apocarotenal 8 having a silyl-protected 19-hydroxy moiety with C(15)-phosphonate 25 bearing a silyl-protected 3-hydroxy-ε-end group. Preparation of apocarotenal 8 was achieved via Stille coupling reaction of alkenyl iodide 10 with alkenyl stananne 9, whereas phosphonate 25 was prepared through treatment of ally alcohol 23 with triethyl phosphite and ZnI(2). The ally alcohol 23 was derived from the known (3R,6R)-3-hydroxy C(15)-aldehyde 20, which was obtained by direct optical resolution of racemate 20 using a semi-preparative chiral HPLC column.
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spelling pubmed-96996172022-11-26 Total Synthesis of Loroxanthin Yamano, Yumiko Tanabe, Mari Shimada, Atsushi Wada, Akimori Mar Drugs Article The first total synthesis of loroxanthin (1) was accomplished by Horner-Wadsworth-Emmons reaction of C(25)-apocarotenal 8 having a silyl-protected 19-hydroxy moiety with C(15)-phosphonate 25 bearing a silyl-protected 3-hydroxy-ε-end group. Preparation of apocarotenal 8 was achieved via Stille coupling reaction of alkenyl iodide 10 with alkenyl stananne 9, whereas phosphonate 25 was prepared through treatment of ally alcohol 23 with triethyl phosphite and ZnI(2). The ally alcohol 23 was derived from the known (3R,6R)-3-hydroxy C(15)-aldehyde 20, which was obtained by direct optical resolution of racemate 20 using a semi-preparative chiral HPLC column. MDPI 2022-10-24 /pmc/articles/PMC9699617/ /pubmed/36354981 http://dx.doi.org/10.3390/md20110658 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yamano, Yumiko
Tanabe, Mari
Shimada, Atsushi
Wada, Akimori
Total Synthesis of Loroxanthin
title Total Synthesis of Loroxanthin
title_full Total Synthesis of Loroxanthin
title_fullStr Total Synthesis of Loroxanthin
title_full_unstemmed Total Synthesis of Loroxanthin
title_short Total Synthesis of Loroxanthin
title_sort total synthesis of loroxanthin
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9699617/
https://www.ncbi.nlm.nih.gov/pubmed/36354981
http://dx.doi.org/10.3390/md20110658
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AT tanabemari totalsynthesisofloroxanthin
AT shimadaatsushi totalsynthesisofloroxanthin
AT wadaakimori totalsynthesisofloroxanthin

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