A Short Synthesis of Vellosimine and Its Derivatives

Rapid access to both enantiomers of vellosimine and itsderivativesis secured from a readily affordable C (2)-symmetric 9-azabicyclo[3.3.1]nonane precursor available in bothenantiomeric forms. The strategy reported leverages desymmetrizationvia intramolecular cyclization used to assemble the key intermediatewith two differentiated carbonyl groups. Late-stage site selectiveindolization enables a concise synthesis of vellosimines and a straightforwarddiversification of the alkaloid scaffold.