Total synthesis of (+)-(8S,13R)-cyclocelabenzine

Article abstract of DOI:10.1002/hlca.19960790506

An asymmetric synthesis of the spermidine alkaloid (+)-cyclocelabenzine(1a) and its (-)-(13S)-epimer 1b is described using optically active (+)-(3S)-3-amino-3-phenylpropionic acid as the chiral building block. The isoquinolin-1-one fragment 15 was synthesized by a modified Bischler-Napieralski reaction. The relative configuration of the (-)-isomer was determined by an X-ray crystal-structure analysis, which enabled us to determine the absolute configuration of natural (+)-1a as (8S,13R).