Synthesis and Chemistry of a Stabilized Dehydrosecodine Model System.

Article abstract of DOI:10.1021/jo00329a029

A stabilized dehydrosecodine analogue bearing carbomethoxy groups in the 3- and 5-positions of the dihydropyridine moiety has been prepared and its chemistry studied.Two novel procedures have been developed for this synthesis: (1) the Lewis acid assisted cleavage of an activated indole ether with trimethylsilylcyanide to form a cyano alcohol and (2) the oxidation of 2-(α-substituted ethyl)indoles with tert-butyl hypochlorite to form the corresponding 2-vinylindole derivatives.Thermal decomposition of the dehydrosecodine analogue does not yield the desired intramole-cular Diels-Alder adducts but instead seems to proceed by an intramolecular hydride transfer from the 1,2-dihydropyridine moiety to the vinylindole group.