Synthesis of the Tricyclic ABC-Ring System of Veratridine.

Abstract

Veratridine is a neurotoxic compound classified into the cevanine group of the Veratrum alkaloids and is characterized by its highly functionalized hexacyclic structure. Here, we report the synthesis of the ABC-ring system of veratridine from a known cis-decalin. The cis-decalin was synthesized from 1,5-pentanediol by modification of a literature method. A site-selective acylation of the C3-hydroxy group with 3,4-dimethoxybenzoyl chloride, a chemo- and stereoselective (allyl)₂Zn-mediated C9-allylation, and ring closing metathesis were employed as key transformations to construct the ABC-ring system of veratridine.