Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction.
The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide addition is used to establish the C17 stereocenter.
Crimmins
Michael T
MT
Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA. crimmins@email.unc.edu
She
Jin
J
D000447:Aldehydes / Q000737:chemistry*; D029061:Annonaceae / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006016:Glycolates / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D023303:Oxazolidinones / Q000737:chemistry; D024301:Plant Bark / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D005663:Furans; D006016:Glycolates; D007783:Lactones; D023303:Oxazolidinones; C064403:gigantecin