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Synlett 1996; 1996(7): 703-704
DOI: 10.1055/s-1996-5552
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En Route to Structural Analogues of Epibatidine: A New Approach Towards 2-Pyridyl-7-oxabicyclo[2.2.1]heptanes

Bernd Sundermann, Hans-Dieter Scharf*
  • *Institut für Organische Chemie, RWTH Aachen, D-52056 Aachen, Germany
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Publication Date:
31 December 2000 (online)

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The synthesis of 2-pyridyl-7-oxabicyclo[2.2.1]heptanes 12, 13, 15 and 16 was accomplished via zinc chloride-mediated Diels-Alder reaction of furan 5 with 2- and 4-vinylpyridine 11 and 14 respectively. 12 and 13 can alternatively be prepared in near quantitative yield by photochemical cyclocotrimerization of nitriles 9 and 10 with acetylene.

2-Pyridyl-7-oxabicyclo[2.2.1]heptanes - Diels-Alder reaction - Lewis acid - photochemical cyclocotrimerization