De Novo Synthesis of the DEF-Ring Stereotriad Core of the Veratrum Alkaloids.

ABSTRACT: The synthesis of the stereotriad core in the eastern portion of the Veratrum alkaloids jervine (1), cyclopamine (2), and veratramine (3) is reported. Starting from a known β-methyltyrosine derivative (8), the route utilizes a diastereoselective substrate-controlled 1,2-reduction to establish the stereochemistry of the vicinal amino alcohol motif embedded within the targets. Oxidative dearomatization is demonstrated to be a viable approach for the synthesis of the spirocyclic DE ring junction found in jervine and cyclopamine.

SUBMITTER: Horwitz MA 

PROVIDER: S-EPMC7246867 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature