Helvetica Chimica Acta p. 1295 - 1304 (1996)
Update date:2022-08-03
Topics:
Schultz
Hesse
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).
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