title: Total synthesis of 8-deshydroxyajudazol B.
abstract: The total synthesis of a stereoisomer of 8-deshydroxyajudazol B (4), the putative biosynthetic intermediate of the ajudazols A (1) and B (2), is described. The key steps in the synthesis included an intramolecular Diels-Alder (IMDA) reaction to secure the isochromanone fragment, a novel selective acylation/O,N-shift to give a hydroxyamide which was cyclized to the oxazole and a high yielding Sonogashira coupling to form the C18-C19 bond. Partial alkyne reduction then afforded the target 4.
authors.affiliation: School of Chemistry, The Bio21 Institute, The University of Melbourne, Victoria 3010, Australia.
authors.forename: Stephen
authors.initials: S
authors.lastname: Birkett
authors.forename: Danny
authors.initials: D
authors.lastname: Ganame
authors.forename: Bill C
authors.initials: BC
authors.lastname: Hawkins
authors.forename: Sébastien
authors.initials: S
authors.lastname: Meiries
authors.forename: Tim
authors.initials: T
authors.lastname: Quach
authors.forename: Mark A
authors.initials: MA
authors.lastname: Rizzacasa
mesh_terms: D000480:Alkynes / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis; D010084:Oxidation-Reduction
chemical_list: C558886:8-deshydroxyajudazol B; D000480:Alkynes; D003374:Coumarins; D010080:Oxazoles; C485091:ajudazol B