ISSN:
1434-193X
Keywords:
Alkaloids
;
Total synthesis/Pumiliotoxin
;
PTX-C
;
PTX isomers
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
