Cyclization of 3-Aminoacrylates – Total Synthesis of Pumiliotoxin C and Related Stereoisomeric Compounds

✍ Scribed by Torsten Riechers; Hans Christoph Krebs; Rudolf Wartchow; Gerhard Habermehl

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 165 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199811)1998:11<2641::aid-ejoc2641>3.0.co;2-u

✦ Synopsis

A method is described for the synthesis of pumiliotoxin C acrylates was transformed into bromide using the tosylate method. Cyclization of the bromides led to unsaturated (1a) and related stereoisomeric compounds 1c-1f. Starting from (+)-or (-)-3-methylcyclohexanone (6a,b), the oxo esters quinoline ring systems. Finally, decarboxylation and catalytic hydrogenation gave the different cis-and trans-fused 7a and 7b were prepared. Condensation with (+)-or (-)-3aminohexanol (8a,b) gave the stereoisomeric 3-amino-stereoisomeric alkaloids of the pumiliotoxin C type. The structures were verified by X-ray analysis. acrylates 9a, 9b and 9c. The hydroxy group of the amino-