Journal article
Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]-octane Building Blocks
In
Journal of Natural Products
—
2000, Volume 63, Issue 5, pp. 592-595
Abstract
The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12 and 13 in 4-5 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
| Language: | English |
|---|---|
| Year: | 2000 |
| Pages: | 592-595 |
| ISSN: | 15206025 and 01633864 |
| Types: | Journal article |
| DOI: | 10.1021/np9905517 |
