The synthesis of several ABE tricyclic analogues 5, 31 and 32 of the alkaloid methyllycaconitine (1) is reported. The analogues contain two key pharmacophores: a tertiary N-(3-phenylpropyl) substituent attached to a 3-azabicyclo-[3.3.1]nonane ring system and a 2-(3-methyl-2,5-dioxopyrrolidin-1-yl)benzoate ester. Double Mannich reaction of the cyclic β-keto esters 6 and 17 with the bis(aminol) ether 7 using methyltrichlorosilane as an activating agent provided an efficient method for the construction of the 3-azabicyclo[3.3.1]nonanes 8 and 18. Ring-closing metathesis of the derived dienes 11, 19, and 20 afforded the tricyclic ethers 12, 21, and 22, respectively, the C-8 ester of which was reduced