Semisynthesis of (−)-Bufospirostenin A Enabled by Photosantonin Rearrangement Reaction
Jun Huang, Tingting Cao, Zhongchao Zhang, Zhen Yang
Abstract
An enantioselective semisynthesis of (-)-bufospirostenin A is described. The key steps in the synthesis involve use of our proposed biomimetic and diastereoselective photosantonin rearrangement reaction for construction of the 5/7 bicyclic motif, and a Co-catalyzed reversible double-bond isomerization reaction for installing the double bond in the seven-membered ring.
Topics & Concepts
SemisynthesisChemistryIsomerizationBicyclic moleculeDouble bondEnantioselective synthesisStereochemistryRing (chemistry)CatalysisCombinatorial chemistryOrganic chemistryMarine Sponges and Natural ProductsMicrobial Natural Products and BiosynthesisTraditional and Medicinal Uses of Annonaceae