Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters.
NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β-unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps starting from (-)-citronellal. The elaboration to the natural product has been investigated using two new approaches. The most successful intercepts our previous work on (-)-7-deoxyloganin (1) allowing completion of a formal total synthesis in 10-steps.
Monash University, Clayton 3800, Melbourne, Australia.
Lisa
L
Candish
David W
DW
Lupton
D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006031:Glycosylation; D039823:Iridoids / Q000138:chemical synthesis*; D007536:Isomerism; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
D004952:Esters; D039823:Iridoids; C030011:carbene; C059516:loganin; D008697:Methane