title: Enantioselective synthesis of an octahydroindolizine (indolizidine) alcohol using an enzymatic resolution.
abstract: A homo-chiral synthesis of (7R,8aS)-octahydro-5,5-dimethylindolizin-7-amine 8 and (7S, 8aS)-octahydro-5,5-dimethylindolizin-7-ol 9, amine building blocks which have found applications within the pharmaceutical industry, is presented. The approach uses a Novozym 435-mediated kinetic resolution of racemic octahydroindolizine (indolizidine) alcohol 13 as a key step (up to 100 g scale).
authors.affiliation: Rigel Pharmaceuticals, 1180 Veterans Boulevard, South San Francisco, CA 94080, USA. mattduncton@yahoo.com.
authors.forename: Jing
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Rigel Pharmaceuticals, 1180 Veterans Boulevard, South San Francisco, CA 94080, USA. mattduncton@yahoo.com.
authors.forename: Rao
authors.initials: R
authors.lastname: Kolluri
authors.affiliation: Rigel Pharmaceuticals, 1180 Veterans Boulevard, South San Francisco, CA 94080, USA. mattduncton@yahoo.com.
authors.forename: Salvador G
authors.initials: SG
authors.lastname: Alvarez
authors.affiliation: Rigel Pharmaceuticals, 1180 Veterans Boulevard, South San Francisco, CA 94080, USA. mattduncton@yahoo.com.
authors.forename: Mark M
authors.initials: MM
authors.lastname: Irving
authors.affiliation: Rigel Pharmaceuticals, 1180 Veterans Boulevard, South San Francisco, CA 94080, USA. mattduncton@yahoo.com.
authors.forename: Rajinder
authors.initials: R
authors.lastname: Singh
authors.affiliation: Rigel Pharmaceuticals, 1180 Veterans Boulevard, South San Francisco, CA 94080, USA. mattduncton@yahoo.com.
authors.forename: Matthew A J
authors.identifier: http://orcid.org/0000-0002-6007-7515
authors.initials: MA
authors.lastname: Duncton
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D054836:Indolizidines; C093667:Novozyme 435; D008049:Lipase