A stereoselective total synthesis of the macrocyclic spermidine alkaloid anhydrocannabisativene (2) has been executed in approximately 17 steps starting from pentadienylsilane 6. The pivotal step in construction of the tetrahydropyridine ring and for establishing the relative stereochemistry of the alkaloid involved an intramolecular imino Diels∼Alder cycloaddition. An intramolecular sulfonamide alkylation was subsequently used to generate the 13-membered macrocyclic lactam ring of 2.
All Science Journal Classification (ASJC) codes
- Colloid and Surface Chemistry