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

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.

Citation

Matthew A Horwitz, Jacob G Robins, Jeffrey S Johnson. De Novo Synthesis of the DEF-Ring Stereotriad Core of the Veratrum Alkaloids. The Journal of organic chemistry. 2020 May 15;85(10):6808-6814

Mesh Tags

Substances

PMID: 32352768

search → result