14-Hydroxytaxodion: Partialsynthese und Reaktionen

Article abstract of DOI:10.1002/hlca.19810640728

The hitherto unknown diterpenoid 14-hydroxytaxodione (10a) has been prepared by oxidation of 6β-hydroxyroyleanone.Its solutions exhibit a dynamic structural behaviour (UV./VIS. and NMR.) and lead to an equilibrium mixture of the 11,14- and the 6,12-dioxo forms.By methylation and acetylation the 6,12-dioxo form can be isolated.Chloroform solutions of 14-hydroxytaxodione slowly set up a mixture of coleon V (2a), coleon U (3) and dimeric products (later established as grandidone C, grandidone D and 7-epigrandidone D).Therefore, coleon V (2a) owing to its strong intramolecular H-bond is more stable than 7,14-dihydroxytaxodione (2b).