Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

Article abstract of DOI:10.1016/0957-4166(96)00199-1

Enantiomerically pure (R)-2-cyclohexen-1-ol 5 was prepared via lipase- catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Diels-Alder reaction and Curtius rearrangement.