Enantiocontrolled Total Synthesis of (−)-Retigeranic Acid A
Xiaoming Chen, Weidong Yao, Hufeng Zheng, Hongyu Wang, Panpan Zhou, Dao‐Yong Zhu, Shao‐Hua Wang
Abstract
The asymmetric total synthesis of (−)-retigeranic acid A has been realized. The key features of the current synthesis include (1) a Pt-catalyzed Conia-ene 5- exo-dig cyclization of enolyne to establish the key quaternary stereochemical center of C-10 (D/E ring), (2) an intramolecular diastereoselective Prins cyclization to construct the trans -hydrindane backbone (A/B ring), and (3) a late-stage intramolecular Fe-mediated hydrogen atom transfer (HAT) Baldwin-disfavored 5- endo - trig radical cyclization to rapidly assemble vicinal quaternary centers and the core structure of (−)-retigeranic acid A (C ring).
Topics & Concepts
ChemistryIntramolecular forceRing (chemistry)StereochemistryTotal synthesisVicinalRadical cyclizationPrins reactionHydrogen atomIntramolecular reactionCatalysisOrganic chemistryGroup (periodic table)Phytochemistry and Bioactivity StudiesMarine Sponges and Natural ProductsAlkaloids: synthesis and pharmacology