Studies on the Constituents of the Seeds of Hernandia ovigera L. II. Several Reactions on the Lignan Components and Their Related Compounds

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Abstract
Two kinds of reactions were carried out on the components of the seeds of H. ovigera L. The reaction of lead tetraacetate on deoxypodophyllotoxin (I) and its analogs caused the cleavage of methylenedioxyl group, affording the corresponding diphenols. In the case of 3,4-methylenedioxypropylbenzene (XII), an intermediate acetoxyl compound was isolated. The reactions of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) on I and its analogs afforded smoothly aromatized compounds. By the same reaction on bursehernin, cyclization and aromatization occurred simultaneously, affording chinensin, which was confirmed by direct comparison with an authentic specimen. The results of the cleavage reaction on I and XII by use of borontrichloride were described.

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