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The structure of ottensinin, a recently reported constituent of the medicinal plant Zingiber ottensii, was revised by re-evaluation of available NMR data from alpha-ylidenebutenolide 1 to gamma-pyrone 2, whose rearranged labdane skeleton is unprecedented. Structure 2 was proven by synthesis from (+)-sclareolide (nine steps, 27% overall yield) and was further validated by X-ray diffraction analysis of our synthetic sample. A plausible biosynthesis of 2 is proposed.
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Boukouvalas et al. (2008) studied this question.
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