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Synthesis of tricyclic analogues of methyllycaconitine using ring closing metathesis to append a B ring to an AE azabicyclic fragment

Barker, David; Brimble, Margaret A; McLeod, Malcolm; Savage, G Paul


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]

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b401119h


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