title: Total synthesis of mycocyclosin.
abstract: The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura-Suzuki cross-coupling to generate the biaryl linkage.
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, VIC 3010, Australia.
authors.forename: James R
authors.initials: JR
authors.lastname: Cochrane
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.forename: Uta
authors.initials: U
authors.lastname: Wille
authors.forename: Craig A
authors.initials: CA
authors.lastname: Hutton
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D054659:Diketopiperazines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry*
chemical_list: D001688:Biological Products; D054659:Diketopiperazines; C573447:mycocyclosin