Irradiation of azides of diterpenoid acids with 1α- and 1β-carboxyl groups gave the corresponding isocyanates and ca. 25% yields of lactams. The azide of hexanoic acid under comparable conditions gave 8% of hexanamide. The reaction has been used to convert podocarpic acid to the enantiomer of the phenol III derived from atisine. This completes the structure proof of the atisine family of alkaloids, the Garrya alkaloids, and related diterpenes, and proves the absolute stereochemistry of these substances.
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ApSimon et al. (1962) studied this question.
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