Starting from 4-bromo-Uhle's ketone (2), an alkylation step using ethyl 3-methylamino-propionate followed by intramolecular aldol condensation in two steps, transformation of the ester group into a methyl group, and finally cyclopropanation of the 8,9 double bond, resulted in a six-step total synthesis of (±)-cycloclavine (1).
- Clavine alkaloids
- Cyclopropanation with diazomethane
- Modified intramolecular Reformatsky-type cyclization
- Total synthesis from 4-bromo-Uhle's ketone
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry