Asymmetric Total Synthesis of (−)-Spirochensilide A
Xin‐Ting Liang, Jiahua Chen, Zhen Yang
Abstract
An asymmetric total synthesis of (-)-spirochensilide A has been achieved for the first time. The synthesis features a semipinacol rearrangement reaction to stereoselectively construct the two-vicinal quaternary chiral centers at C8 and C10, a tungsten-mediated cyclopropene-based Pauson-Khand reaction to install the C13 quaternary chiral center, and a furan-based oxidative cyclization to stereoselectively form the spiroketal motif.
Topics & Concepts
ChemistryCyclopropeneVicinalTotal synthesisStereochemistryFuranStereoselectivityQuaternary carbonEnantioselective synthesisCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisAsymmetric Synthesis and CatalysisTraditional and Medicinal Uses of AnnonaceaeSynthetic Organic Chemistry Methods