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

The stereoselective synthesis of C40-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 C15-5,6-...

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Published inJournal of natural products (Washington, D.C.) Vol. 85; no. 10; pp. 2302 - 2311
Main Authors Rivas, Aurea, Castiñeira, Marta, Álvarez, Rosana, Vaz, Belén, de Lera, Angel R.
Format Journal Article
LanguageEnglish
Published American Chemical Society and American Society of Pharmacognosy 28.10.2022
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Summary:The stereoselective synthesis of C40-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 C15-5,6-epoxycyclohexadienyl­phosphonate and a central C10-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.
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ISSN:0163-3864
1520-6025
1520-6025
DOI:10.1021/acs.jnatprod.2c00475