-OXOHEXAHYDROINDOLIZINO[8,7-B]INDOLE-5-CARBOXYLATE DERIVATIVES AS NEWSCAFFOLDS FOR MIMICKING BETA-TURN SECONDARY STRUCTURES - MOLECULAR-DYNAMICS AND STEREOSELECTIVE SYNTHESIS
N. Delafiguera et al., -OXOHEXAHYDROINDOLIZINO[8,7-B]INDOLE-5-CARBOXYLATE DERIVATIVES AS NEWSCAFFOLDS FOR MIMICKING BETA-TURN SECONDARY STRUCTURES - MOLECULAR-DYNAMICS AND STEREOSELECTIVE SYNTHESIS, Tetrahedron, 51(28), 1995, pp. 7841-7856
Highly constrained -oxohexahydroindolizino[8-7-b]indole-5-carboxylate
derivatives of general formula 1 have been developed as novel beta-tur
n mimetics. Molecular dynamics studies on model structures 2a and 2b h
ave revealed that both indolizinoindole derivatives are able to adopt
conformations close to those of ideal type II' beta-turn. The asymmetr
ic synthesis of this heterocyclic system was accomplished from 1,3-di-
and 1,2,3-trisubstituted tetrahydro-beta-carbolines, which were prepa
red in stereoselective or stereospecific way by application of the Pic
tet-Spengler reaction.