title: Total Synthesis and Structural Revision of Antibiotic CJ-16,264.
abstract: The total synthesis and structural revision of antibiotic CJ-16,264 is described. Starting with citronellal, the quest for the target molecule featured a novel bis-transannular Diels-Alder reaction that casted stereoselectively the decalin system and included the synthesis of six isomers before demystification of its true structure.
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA). kcn@rice.edu.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA).
authors.forename: Akshay A
authors.initials: AA
authors.lastname: Shah
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA).
authors.forename: Henry
authors.initials: H
authors.lastname: Korman
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA).
authors.forename: Tabrez
authors.initials: T
authors.lastname: Khan
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA).
authors.forename: Lei
authors.initials: L
authors.lastname: Shi
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA).
authors.forename: Wisuttaya
authors.initials: W
authors.lastname: Worawalai
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093 (USA).
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; C000607271:CJ-16,264; D007783:Lactones; D009281:Naphthalenes; D011720:Pyrazoles; C007229:decalin
keywords: antibiotic; natural products; structural revision; total synthesis; transannular Diels-Alder reaction