Total Synthesis of Spiro[cyclohexane-2-indoline] Alkaloids: A Regio- and Diastereoselective Spirocyclization Approach
Angewandte Chemie International Edition(2022)
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.
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Key words
Indolines,Kopsia Alkaloids,Spiro Compounds,Spirocyclization,Total Synthesis
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