AZABICYCLO[3.2.1]OCTENE DERIVATIVES OBTAINED BY REARRANGEMENT REACTIONS IN COURSE OF THE CATHARANTHINE SYNTHESIS

In the course of our synthesis of the alkaloid catharanthine 1a (2-->4 -->6-->1)2,3, allocatharanthine 1b and deethylcatharanthine 1c, severa l azabicyclo [3.2.1]octene derivatives were obtained by rearrangement of the isoquinuclidine ring system. The structures and sterochemistry of the azabicyclo[3.2.1]octene derivatives were determined by various NMR methods (NOE and two-dimensional INEPT experiments).