Dearomatization of Indole via Intramolecular [3 + 2] Cycloaddition: Access to the Pentacyclic Skeleton of Strychons Alkaloids

Organic Letters
Zhengshen WangHuaiji Zheng

Abstract

An efficient method to build various multisubstituted polycyclic indoline-annulated normal to medium-size rings through dearomatization of indole via a tandem 1,2-acyloxy migration/intramolecular [3 + 2] cycloaddition process is described. The pentacyclic skeleton of strychnine could be synthesized via this tandem cycloaddition and a further Mannich reaction. This approach would provide a novel strategy to the synthesis of strychons alkaloids.

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