RT Journal Article
T1 Stereoselective Synthesis of Bisfuranoxide (Aurochrome, Auroxanthin) and Monofuranoxide (Equinenone 5′,8′-Epoxide) Carotenoids by Double Horner–Wadsworth–Emmons Reaction
A1 Rivas Landin, Aurea
A1 Castiñeira Reis, Marta
A1 Álvarez Rodríguez, Maria Rosana
A1 Vaz Araujo, Belén
A1 Rodríguez de Lera, Ángel
K1 2306.90 Química de Productos Naturales Orgánicos
AB 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.
PB Journal of Natural Products
SN 01633864
YR 2022
FD 2022-10-28
LK http://hdl.handle.net/11093/4156
UL http://hdl.handle.net/11093/4156
LA eng
NO Journal of Natural Products, 85(10): 2302-2311 (2022)
NO Financiado para publicación en acceso aberto: Universidade de Vigo/CISUG
NO Xunta de Galicia | Ref. ED-431G/02-FEDER
DS Investigo
RD 14-ene-2025