Total Synthesis of the Alleged Structure of (+)-Fimbricalyxoid A
Linping Li, Jia-Qi Han, F. Yang, Wu Xiong, Jian‐Hua Xie, Qi‐Lin Zhou
Abstract
An enantioselective total synthesis of the alleged structure of (+)-fimbricalyxoid A is reported. The synthetic strategy features a pyridine-N-oxidate-mediated SN2′ reaction to introduce an oxygen functionality at position C3 of the A-ring and a sequential three-step process via the cleavage of the C–O bonds and hemiketalization to form the 3,20-oxybridge. With this strategy, the target molecule was synthesized in 19% overall yield and 12 steps from our previously synthesized cis-fused octahydrophenanthrene (+)-6.
Topics & Concepts
ChemistryEnantioselective synthesisSN2 reactionYield (engineering)PyridineTotal synthesisRing (chemistry)Cleavage (geology)MoleculeStereochemistryCombinatorial chemistryCatalysisMedicinal chemistryOrganic chemistryFracture (geology)Materials scienceEngineeringGeotechnical engineeringMetallurgyBioactive Natural Diterpenoids ResearchTraditional and Medicinal Uses of AnnonaceaeBiological Activity of Diterpenoids and Biflavonoids