Synthesis of the polycyclic ring systems of artocarpol A and D.
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]
Paduraru
M Peggy
MP
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada V5A 1S6.
Wilson
Peter D
PD
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis; D031622:Artocarpus / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure
D000893:Anti-Inflammatory Agents; D006576:Heterocyclic Compounds, 4 or More Rings; C492477:artocarpol A; C492478:artocarpol D