ChemInform Abstract: Synthesis Studies Directed Toward Gelsemine. A New Synthesis of Highly Functionalized cis-Hydroisoquinolines.

ChemInform Abstract

Diels-Alder reaction of the oxycyclohexadienes (I) with methyl acrylate (II) forms the bicyclic esters (III) which are converted to the amines (VI) and (VII) via the carbamates (V). (IIIb) is oxidized and olefinated, producing the vinyl analogue (IX) which is similarly transformed into the amine (X). (VI) undergoes ring closure with formaldehyde (XI), yielding the tetracyclic compound (XII). The amines (VII) and (X) are cyanomethylated and then subjected to base-induced rearrangement, giving isoquinoline derivatives such as (XVI) and (XX).