Enantioselective synthesis of an octahydroindolizine (indolizidine) alcohol using an enzymatic resolution

Enantioselective synthesis of an octahydroindolizine (indolizidine) alcohol using an enzymatic resolution

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 rac...

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Veröffentlicht in:Organic & biomolecular chemistry 2017-04, Vol.15 (14), p.2953-2961
Hauptverfasser: Zhang, Jing, Kolluri, Rao, Alvarez, Salvador G, Irving, Mark M, Singh, Rajinder, Duncton, Matthew A J
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Biocatalysis
Chemistry Techniques, Synthetic
Indolizidines - chemical synthesis
Indolizidines - chemistry
Kinetics
Lipase - metabolism
Models, Molecular
Molecular Conformation
Stereoisomerism
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Zusammenfassung: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).
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00192d