Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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.
Originalsprog | Engelsk |
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Tidsskrift | Journal of Natural Products |
Vol/bind | 63 |
Udgave nummer | 5 |
Sider (fra-til) | 592-5 |
Antal sider | 4 |
ISSN | 0163-3864 |
Status | Udgivet - 2000 |
Eksternt udgivet | Ja |
ID: 43211704