Total Synthesis of (−)-Retigeranic Acid A: A Reductive Skeletal Rearrangement Strategy
Dongyu Sun, Ruyi Chen, Dongmin Tang, Qi‐Dong Xia, Yifan Zhao, Chunhui Liu, Hanfeng Ding
Abstract
The asymmetric total synthesis of (-)-retigeranic acid A was described, which relies on a crucial reductive skeletal rearrangement cascade for the controllable assembly of diverse angular triquinane subunits. Taken together with an intramolecular Michael/aldol cyclization, an ODI-[5 + 2] cycloaddition/pinacol rearrangement cascade, a Wolff ring contraction and a stereoselective HAT reduction, our synthetic approach has enabled the access to (-)-retigeranic acid A in a concise and practical manner.
Topics & Concepts
ChemistryAldol reactionIntramolecular forceStereoselectivityTotal synthesisStereochemistryCascadeCycloadditionCombinatorial chemistryOrganic chemistryCatalysisChromatographyAlkaloids: synthesis and pharmacologyPlant Toxicity and Pharmacological PropertiesMarine Sponges and Natural Products