Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
UNIVERSAL IDENTIFIER: http://hdl.handle.net/11093/4156
EDITED VERSION: https://pubs.acs.org/doi/10.1021/acs.jnatprod.2c00475
UNESCO SUBJECT: 2306.90 Química de Productos Naturales Orgánicos
DOCUMENT TYPE: article
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.
Files in this item
- 2022_rivas_stereoselective_syn ...