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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Detalles Bibliográficos
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
Descripción
Sumario: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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