A biomimetic transformation of serratinine into serratezomine A through a modified Polonovski reaction.
Application of a modified Polonovski reaction for serratinine (1) resulted in generation of serratezomine A (2) with a novel seco-serratinine-type skeleton recently isolated from the club moss Lycopodium serratum var. serratum. This biomimetic transformation supports a biogenetic pathway proposed for serratezomine A (2). The absolute stereochemistry of serratezomine A (2) was established by an induced exciton chirality and modified Mosher methods.
Morita
Hiroshi
H
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Kobayashi
Jun'ichi
J
D000470:Alkaloids / Q000737:chemistry*; D002384:Catalysis; D007212:Indolizines / Q000737:chemistry*; D029542:Lycopodiaceae / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
D000470:Alkaloids; D007212:Indolizines; C415194:serratezomine A; C009245:serratinine