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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of the polycyclic ring systems of artocarpol A and D
M Peggy Paduraru1, Peter D Wilson
1Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada V5A 1S6.
Abstract:
The first synthesis of the polycyclic ring systems of artocarpol A and D has been accomplished. These natural products were isolated recently from the root bark of Artocarpus rigida, and artocarpol A has been shown to have potent antiinflammatory properties. The synthesis of an artocarpol D analogue was achieved on condensation of 11H-dibenzo[b,f]oxepin-10-one with senecialdehyde. The reaction of this oxepinone with citral afforded a 2H-pyran that on subsequent irradiation afforded an analogue of artocarpol A. [reaction: see text]
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