A Short Synthesis of Vellosimine and Its Derivatives
Barbara Chatinovska1, Rokas Gegevičius1, Edvinas Orentas1
1Department of Organic Chemistry, Institute of Chemistry, Vilnius University, Naugarduko 24, LT-03225 Vilnius, Lithuania.
Abstract:
Rapid access to both enantiomers of vellosimine and its derivatives is secured from a readily affordable C2-symmetric 9-azabicyclo[3.3.1]nonane precursor available in both enantiomeric forms. The strategy reported leverages desymmetrization via intramolecular cyclization used to assemble the key intermediate with two differentiated carbonyl groups. Late-stage site selective indolization enables a concise synthesis of vellosimines and a straightforward diversification of the alkaloid scaffold.
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