Synthesis of tricyclic analogues of methyllycaconitine using ring closing metathesis to append a B ring to an AE azabicyclic fragment
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Barker, David; Brimble, Margaret A; McLeod, Malcolm; Savage, G Paul
Description
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]
Collections | ANU Research Publications |
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Date published: | 2004 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/53121 |
Source: | Organic and Biomolecular Chemistry |
DOI: | 10.1039/b401119h |
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