A chiral synthesis of (-)-cannabisativine: An application of the highly diastereo-selective hetero Diels-Alder reaction

Article abstract of DOI:10.1016/S0040-4039(00)74295-X

The polyamine alkaloid cannabisativine was synthesized as an optical active form. The key step is the hetero Diels-Alder reaction of chiral diene and an N-tosylimine, in which regio- and diastereo-face selectivities were completely controlled, only one diastereomer was isolated in high yield. Synthesized (-)-cannabisativine has the same physical data as the natural product except for the αD value.