✦ LIBER ✦

Synthesis of Semi-Rigid Analogs of Anabasine

✍ Scribed by Steven W. Szczepanski; Katherine G. Anouna

Publisher: Elsevier Science
Year: 1996
Tongue: French
Weight: 240 KB
Volume: 37
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02058-8

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✦ Synopsis

The synthesis of 3-(3-pyridyl)-2-azabicyclo[2.2.2]octane 1, a semi-rigid analog of anabasine, is reported. This compound is prepared via Lewis acid promoted imino Diels-Alder reaction of 3-pyridine bismethylcarbamate 7 with 1,3-cyclohexadiene to form the rigid azabicyclic backbone. A 6-chloropyridyl analog 2 is also prepared. Hydrogenation and deprotection provide the desired substrates.

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