title: Total synthesis and absolute configuration of curvularides A-E.
abstract: The first total synthesis of curvularides A-E, isolated from a culture broth of the endophytic fungus Curvularia geniculata, is described. The divergent total synthesis reported herein confirmed the absolute configurations of curvularides A-E and supported that these natural products might be obtained from a common biosynthetic pathway. The key steps involved in the synthesis were the diastereoselective hydrogenation of exo-methylene-γ-butyrolactone to α-methyl-γ-butyrolactone, Sharpless kinetic resolution, Sharpless asymmetric epoxidations, and intramolecular and intermolecular epoxide openings.
authors.affiliation: Division of Crop Protection Chemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India. gsudhakar@iict.res.in
authors.forename: Gangarajula
authors.initials: G
authors.lastname: Sudhakar
authors.forename: Kovela
authors.initials: K
authors.lastname: Satish
authors.forename: Jakka
authors.initials: J
authors.lastname: Raghavaiah
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D005658:Fungi / Q000737:chemistry*; D006865:Hydrogenation; D007700:Kinetics; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D004852:Epoxy Compounds; D010455:Peptides; C554505:curvularide B; D015107:4-Butyrolactone