Abstract
The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.
| Original language | English |
|---|---|
| Journal | Journal of Natural Products |
| Volume | 63 |
| Issue number | 5 |
| Pages (from-to) | 592-5 |
| Number of pages | 4 |
| ISSN | 0163-3864 |
| Publication status | Published - 2000 |
| Externally published | Yes |
Keywords
- Aza Compounds
- Bicyclo Compounds
- Glucosides
- Hypoglycemic Agents
- Indicators and Reagents
- Iridoid Glucosides
- Iridoids
- Pyrans
- Substance P