title: Total Synthesis of Trioxacarcins DC-45-A1, A, D, C, and C7″-epi-C and Full Structural Assignment of Trioxacarcin C.
abstract: Trioxacarcins DC-45-A2, DC-45-A1, A, D, C7″-epi-C, and C have been synthesized through stereoselective strategies involving BF3·Et2O-catalyzed ketone-epoxide opening and gold-catalyzed glycosylation reactions, and the full structural assignment of trioxacacin C was deciphered via the syntheses of both of its C7″ epimers. The gathered knowledge sets the foundation for the design, synthesis, and biological evalution of analogues of these natural products as potential payloads for antibody-drug conjugates and other delivery systems for targeted and personalized cancer chemotherapy.
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
authors.forename: Quan
authors.initials: Q
authors.lastname: Cai
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
authors.forename: Hongbao
authors.initials: H
authors.lastname: Sun
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
authors.forename: Bo
authors.initials: B
authors.lastname: Qin
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
authors.forename: Shugao
authors.initials: S
authors.lastname: Zhu
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D013237:Stereoisomerism
chemical_list: D000617:Aminoglycosides; C033790:trioxacarcin