Abstract

Keto acid (VII) was assumed to be a precursor in the biogenesis of levantenolides (IV and V). The syntheses of the analogous compounds (IX and X) and their cyclization to IV and V were carried out as follows. Reaction of farnesyl bromide (XV and XX) with 2,2′-di-3-methylfurylmercury afforded the corresponding furano derivatives (XVI and XXI), which were photo-oxidized to butenolide derivatives (IX and X). Biogenetic-type cyclization of IX and X with stannic chloride afforded IV, V, and XIX in moderate yields.

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