The compact tricyclic substructure of solanoeclepin A containing the cyclobutanone ring was prepared by using as the key step a highly regioselective intramolecular [2 + 2]-photocycloaddition reaction between one of the [small pi]-bonds of an allene and the CC double bond of a butenolide.
Synthesis of the Cyclobutanone Core of Solanoeclepin A via Intramolecular Allene Butenolide Photocycloaddition. -Title compound (I) is a potent hatching agent of potato cyst nematodes. -(HUE, B. T. B.; DIJKINK, J.; KUIPER, S.; LARSON, K. K.; GUZIEC, F. S. J.; GOUBITZ, K.; FRAANJE, J.; SCHENK, H.; VAN MAARSEVEEN, J. H.; HIEMSTRA*, H.; Org. Biomol. Chem. 1 (2003) 24, 4364-4366; Inst. Mol. Chem., Univ. Amsterdam, NL-1018 WS Amsterdam, Neth.; Eng.) -Nuesgen 20-029
Studies are reported towards the synthesis of solanoeclepin A (1), the hatching agent of potato cyst nematodes. Two approaches are investigated to access the tricyclic core including the intricate bicyclo[2.1.1]hexanone moiety. The first approach is based on the intramolecular [2+2] photocycloaddition of dioxenone butenolide 10 and is shown to be less practical due to the limited synthetic utility of the photoproduct 11. The second approach uses as the key step the intramolecular [2+2] photocycloaddition reaction of allene butenolide 39. This latter photosubstrate is prepared through silver-mediated coupling of silyloxyfuran 9 and allenic bromide
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