Conversion of the iridoid glucoside antirrhinoside into 3-azabicyclo[3.3.0]octane building blocks.
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.
Franzyk
H
H
Department of Organic Chemistry, The Technical University of Denmark, Building 201, DK-2800, Lyngby, Denmark. okhf@pop.dtu.dk
Frederiksen
S M
SM
Jensen
S R
SR
D001372:Aza Compounds / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D007004:Hypoglycemic Agents / Q000737:chemistry; D007202:Indicators and Reagents; D057888:Iridoid Glucosides; D039823:Iridoids; D011714:Pyrans / Q000737:chemistry*; D013373:Substance P / Q000037:antagonists & inhibitors
D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D005960:Glucosides; D007004:Hypoglycemic Agents; D007202:Indicators and Reagents; D057888:Iridoid Glucosides; D039823:Iridoids; D011714:Pyrans; C410909:iridoid glucoside antirrhinoside; D013373:Substance P