Premium
Cyclization of 3‐Aminoacrylates – Total Synthesis of Pumiliotoxin C and Related Stereoisomeric Compounds
Author(s) -
Riechers Torsten,
Krebs Hans Christoph,
Wartchow Rudolf,
Habermehl Gerhard
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2641::aid-ejoc2641>3.0.co;2-u
Subject(s) - chemistry , decarboxylation , quinoline , bromide , ring (chemistry) , enantioselective synthesis , stereochemistry , catalysis , organic chemistry , medicinal chemistry
Abstract A method is described for the synthesis of pumiliotoxin C ( 1a ) and related stereoisomeric compounds 1c – 1f . Starting from (+)‐ or (–)‐3‐methylcyclohexanone ( 6a , b ), the oxo esters 7a and 7b were prepared. Condensation with (+)‐ or (–)‐3‐aminohexanol ( 8a , b ) gave the stereoisomeric 3‐aminoacrylates 9a , 9b and 9c . The hydroxy group of the amino‐acrylates was transformed into bromide using the tosylate method. Cyclization of the bromides led to unsaturated quinoline ring systems. Finally, decarboxylation and catalytic hydrogenation gave the different cis ‐ and trans ‐fused stereoisomeric alkaloids of the pumiliotoxin C type. The structures were verified by X‐ray analysis.