A novel short convergent entry into himbacine derivatives.
[reaction: see text]. The IMDA reaction of 9 leads with good stereoselectivity to exo-adduct 10b. The functionalized ABC-ring core in 10 is well suited for the convergent synthesis of analogues of himbacine, a naturally occurring M2 selective muscarine receptor antagonist, as illustrated with the further synthesis of the dehydro-derivative 5.
Van Cauwenberge
Gunther
G
Department of Organic Chemistry, Ghent University, Krijgslaan 281, B-9000 Gent, Belgium.
Gao
Ling-Jie
LJ
Van Haver
Dirk
D
Milanesio
Marco
M
Viterbo
Davide
D
De Clercq
Pierre J
PJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001315:Australia; D018360:Crystallography, X-Ray; D005663:Furans; D007202:Indicators and Reagents; D008958:Models, Molecular; D018727:Muscarinic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D009281:Naphthalenes; D009512:New Guinea; D010880:Piperidines; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D005663:Furans; D007202:Indicators and Reagents; D018727:Muscarinic Antagonists; D009281:Naphthalenes; D010880:Piperidines; C048172:himbacine