124563-69-5Relevant academic research and scientific papers
General Method for the Synthesis of Bridged Indole Alkaloids. Nucleophilic Addition of Indoleacetic Ester Enolates to N-Alkylpyridinium Salts
Bennasar, M.-Lluisa,Alvarez, Mercedes,Lavilla, Rodolfo,Zulaica, Ester,Bosch, Joan
, p. 1156 - 1168 (1990)
A short route to tetracyclic ring substructures of C-mavacurine, Strychnos, and akuammiline-type alkaloids, based on the addition of methyl 1-, 2-, or 3-indoleacetate anions to N-alkylpyridinium salts followed by acid cyclization of the resultant 1,4-dihydropyridines, is reported.Further stereoselective elaboration of the C-20 (E)-ethylidene substituent results in the synthesis of the indole alkaloid vinoxine (7b) and of 4-ethylidene-hexahydro-1,5-methanoazocino- and -indoles 14-17, 32, and 35.Some mechanistic aspects concerning the regiochemistry of the nucleophilic addition to the pyridinium ring are discussed.
