High yielding and remarkably selective alkylations of a suitably protected derivative of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid are described. The fused bicyclic structure of this proline analogue greatly influences the stereochemical outcome of direct alkylation reactions taking place at the alpha-carbon and provides access to alpha-substituted analogues with retention of the configuration. The overall procedure allows the preparation of enantiopure alpha-substituted derivatives of this Oic isomer, suitably protected for their incorporation into peptides, in a straightforward manner.
High yielding and remarkably selective alkylations of a suitably protected derivative of n class="Chemical">(2S,3aS,7aS)-octahydroindole-2-carboxylic acid are described. The fused bicyclic structure of this proline analogue greatly influences the stereochemical outcome of direct alkylation reactions taking place at the alpha-carbon and provides access to alpha-substituted analogues with retention of the configuration. The overall procedure allows the preparation of enantiopure alpha-substituted derivatives of this Oic isomer, suitably protected for their incorporation into peptides, in a straightforward manner.
Authors: Robert B Perni; Gurudatt Chandorkar; Kevin M Cottrell; Cynthia A Gates; Chao Lin; Kai Lin; Yu-Ping Luong; John P Maxwell; Mark A Murcko; Janos Pitlik; Govinda Rao; Wayne C Schairer; John Van Drie; Yunyi Wei Journal: Bioorg Med Chem Lett Date: 2007-04-03 Impact factor: 2.823
Authors: C J Blankley; J S Kaltenbronn; D E DeJohn; A Werner; L R Bennett; G Bobowski; U Krolls; D R Johnson; W M Pearlman; M L Hoefle Journal: J Med Chem Date: 1987-06 Impact factor: 7.446