Synthesis of plagiochiline N from santonin

Article abstract of DOI:10.1021/jo010567d

This article reports the transformation of O-acetylisophotosantonin, obtained by photochemical rearrangement of santonin, into plagiochiline N, an ent-2,3-secoaromadendrane isolated from Plagiochila ovalifolia. The synthesis was carried out in a sequence involving as the key steps (a) the substitution of the lactone moeity by a gem-dimethylcyclopropane ring through a synthetic intermediate having a C₆-C₇ double bond and (b) the ozonolysis of the C₂-C₃ bond followed by cyclization to the dihydropyran ring characteristic of plagiochiline N. Spectroscopic data of the synthetic product fully coincide with the reported data for the natural product.