Some biogenetic-type transformations of neoclerodane diterpenoids from Scutellaria species.
Treatment of scutebaicalin (1) with K-t-BuO yielded both the (13S)- and (13R)-8beta,13-epoxyclerodanes 2 and 3, respectively, by a Michael-type heterocyclization reaction. Identical treatment of scutalpin B (4) gave the corresponding (11E)-11-deacetoxy-12-dehydro derivative 5 by an elimination reaction. Side chains at C-9, such as those of compounds 1-5, are frequent among the neoclerodanes found in Scutellaria species, and these transformations suggest a plausible biogenetic pathway for these diterpenoids.
Hussein
A A
AA
Instituto de Química Orgánica, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, E-28006 Madrid, Spain.
Muñoz
D M
DM
de la Torre
M C
MC
Rodríguez
B
B
D002240:Carbohydrate Sequence; D004224:Diterpenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D004224:Diterpenes