Novel sparteine-mediated enantio-dichotomic formal synthesis of R-(-)- and S-(+)-curcuphenol.
High and opposite enantiodiscriminations were observed between tertiary amides and secondary amides in the sparteine-mediated lateral metalation-allylation of 2-ethyl-m-toluamide derivatives (2a, 2e). The results described above have been applied for the formal synthesis of both enantiomers of curcuphenol. The brief mechanistic studies suggested that stereoinformation was introduced after the deprotonation step.
Kimachi
T
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku 606-8501, Kyoto, Japan. tkimachi@pharm.kyoto-u.ac.jp
Takemoto
Y
Y
D000818:Animals; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013034:Sparteine / Q000378:metabolism*; D013237:Stereoisomerism
D012717:Sesquiterpenes; D013034:Sparteine; C054389:curcuphenol