On the constituents of Linaria japonica Mig. IV. Chemical correlation of cis-clerodane diterpenes with trans-clerodane diterpenes

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  • On the constituents of Linaria japonica Miq. IV. Chemical correlation of cis-clerodane diterpenes with trans-clerodane diterpenes.

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The chemical correlation between 5α-methyl-trans-clerodane diterpenes and 5β-methyl-cis-clerodane diterpenes was investigated. Attempts to correlate a trans-clerodane [e.g. methyl kolavenate (1)] with a cis-clerodane by virtue of i) photoisomerization of a 19-nor-4-keto derivative (6) of 1 and ii) photoisomerization of a related transhydrindanone derivative (14=18), were unsuccessful. However, an interrelation, by virtue of photolysis of a 19-nor-4-keto derivative (26) of cis-clerodane [e.g. linaridial (19)] leading to 6, was successful. This is the first report of a chemical correlation between cis-and trans-clerodane diterpenes. The stereochemical course of the photoisomerization observed for cis-19-nor-4-ketone (26) leading to its trans isomer (6) is discussed.

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