Synthesis of tricyclic analogues of methyllycaconitine using ring closing metathesis to append a B ring to an AE azabicyclic fragment
The synthesis of several ABE tricyclic analogues of the alkaloid methyllycaconitine 1 is reported. The analogues contain two key pharmacophores: a homocholine motif formed from a tertiary N-ethyl amine in a 3-azabicyclo-[3.3.1]nonane ring system and a 2-(3-methyl-2,5-dioxopyrrolidin-1- ly)benzoate ester. The synthesis of the ABE tricyclic analogues of MLA1 began with selective allylation at C-3 of 3 to produce allyl β-keto ester 4. Double Mannich reaction of 4 with ethylamine and formaldehyde...[Show more]
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