Abstract
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.
Original language | English (US) |
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Pages (from-to) | 3240-3245 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 106 |
Issue number | 11 |
DOIs | |
State | Published - Nov 1984 |
All Science Journal Classification (ASJC) codes
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry