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

D Barker, MA Brimble, MD McLeod…

Index: Barker, David; Brimble, Margaret A; McLeod, Malcolm D; Savage, G Paul Organic and biomolecular chemistry, 2004 , vol. 2, # 11 p. 1659 - 1669

Full Text: HTML

Citation Number: 22

Abstract

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 MLA 1 began with selective allylation at C-3 of 3 to produce allyl β-keto ester 4. Double ...