Journal
JOURNAL OF NATURAL PRODUCTS
Volume 85, Issue 10, Pages 2302-2311Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.2c00475
Keywords
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Funding
- Spanish MINECO [PID2019-107855RB-I00-FEDER]
- AEI
- Xunta de Galicia (Consolidacion GRC )
- DXPCTSUG [ED431C 2017/61]
- Unha maneira de facer Europa [PID2019-107855RB-I00-FEDER]
- Galician Research Center 2016-2019
- [ED-431G/02-FEDER]
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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.
The stereoselective synthesis of C40-all-trans- carotenoids with the formal hexahydrobenzofuran skeletons aurochrome, auroxanthin, and equinenone-5'8'-epoxide is re-ported. 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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