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.
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
Michael T
MT
Crimmins
Jin
J
She
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