# Enantioselective Synthesis of the Guaipyridine Alkaloid (+)- and (−)-Cananodine

## TL;DR

Scientists synthesized both enantiomers of the guaipyridine alkaloid cananodine using specific chemical reactions, confirming their structures and enabling future analogue development.

## Contribution

A new synthetic route for both enantiomers of cananodine using stereoselective reactions and confirming optical rotations.

## Key findings

- The stereocenter at C8 was established via Evans alkylation.
- A seven-membered carbocycle was formed using an intramolecular Mizoroki–Heck reaction.
- The C5 stereocenter was set through hydrogenation of an exomethylene.

## Abstract

Synthesis of both
enantiomers of guaipyridine alkaloid cananodine
was achieved. The stereocenter at C8 was set through an Evans alkylation,
and the seven-membered carbocycle was constructed using an intramolecular
Mizoroki–Heck reaction. Hydrogenation of an exomethylene set
the C5 stereocenter. The optical rotation of each enantiomer matched
the literature. The synthetic scheme is amenable to analogue preparation.
(+)- and (−)-Rupestine G were also prepared.