A short and general synthesis for the preparation of various conformationally constrained β- substituted tryptophans has been elaborated starting from indole, aldehydes and Meldrum's acid by using trimolecular condensation and Curtius rearrangement mediated functional group transformations followed by deprotections, as key-steps. The relative configurations of the two diastereomeric series have been determined indirectly by the measurement of 3J ...