Bioinspired Synthesis of Nortriterpenoid Propindilactone G
Yu Wang, Bo Chen, Xubiao He, Jinghan Gui
Abstract
nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suárez remote radical functionalization, a ring expansion enabled by a Wagner-Meerwein rearrangement, a stereoinversion of a tertiary alcohol, and a biomimetic transesterification/oxa-Michael addition cascade. This work also provides experimental evidence of the putative propindilactone G biosynthesis pathway.
Topics & Concepts
ChemistrySurface modificationBiomimetic synthesisStereochemistryPolyketideTotal synthesisLactoneTransesterificationBiosynthesisCombinatorial chemistryOrganic chemistryCatalysisEnzymePhysical chemistryPlant-derived Lignans Synthesis and BioactivityCyclopropane Reaction MechanismsTraditional and Medicinal Uses of Annonaceae