Total Synthesis of Spiro[cyclohexane‐2‐indoline] Alkaloids: A Regio‐ and Diastereoselective Spirocyclization Approach
Lu Chen, Kejing Xie, Jingyang Zhang, Liansuo Zu
Abstract
A direct spirocyclization approach for the chemical synthesis of spiro[cyclohexane-2-indoline] alkaloids is reported. The absolute stereochemistry was introduced by a desymmetrizing Dieckmann condensation, and the relative stereochemistry was controlled by the manipulation of the kinetic and thermodynamic pathways of the spirocyclization. By contrast to the biogenetic proposal involving the diester-type alkaloid as the precursor, we demonstrate that chemically a common lactone-type intermediate could bridge the chemical synthesis of this class of natural products.
Topics & Concepts
IndolineCyclohexaneChemistryStereochemistryTotal synthesisAlkaloidLactoneCondensationChemical synthesisOrganic chemistryBiochemistryThermodynamicsPhysicsIn vitroAlkaloids: synthesis and pharmacologyTraditional and Medicinal Uses of AnnonaceaeChemical synthesis and alkaloids