Catalytic Asymmetric Total Synthesis of Exiguolide
Kengo Oka, Shunsuke Fuchi, Keita Komine, Hayato Fukuda, Susumi Hatakeyama, Jun Ishihara
Abstract
The catalytic asymmetric total synthesis of (-)-exiguolide, a complex 20-membered macrolide embedded with a bis(tetrahydropyran) motif, is reported. The convergent synthesis involves the construction of the C1-C11 tetrahydropyran segment via catalytic asymmetric allylation and Prins cyclization, and the formation of the C12-C21 phosphonate segment via catalytic asymmetric cyclocondensation reaction and Johnson-Claisen rearrangement. The synthesis of 15-epi-exiguolide is also described.
Topics & Concepts
TetrahydropyranPrins reactionCatalysisEnantioselective synthesisPhosphonateChemistryTotal synthesisStereochemistryCombinatorial chemistryOrganic chemistryRing (chemistry)Synthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisChemical synthesis and alkaloids