Organic Chemistry

Total Syntheses of the C19 Diterpenoid Alkaloids (–)-Talatisamine, (–)-Liljestrandisine, and (–)-Liljestrandinine by a Fragment Coupling Approach

Sarah Reisman California Institute of Technology

Abstract

The C19 aconitine-type diterpenoid alkaloids (–)-talatisamine, (–)-liljestrandisine, and (–)-liljestrandinine have been prepared in 31, 30, and 33 steps, respectively, from phenol. The synthetic approach features a 1,2-addition/semi-pinacol rearrangement as the key fragment coupling tactic. These efforts have also resulted in a correction to the original structure assignment of (–)-liljestrandisine.

Version notes

version updated 5/5/21

Content

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Supplementary material

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2020-04-30 ARW NJF SI