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
Original language | English |
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Journal | Journal of Natural Products |
Volume | 63 |
Issue number | 5 |
Pages (from-to) | 592-595 |
ISSN | 0163-3864 |
Publication status | Published - 2000 |