title: Total synthesis of the photoprotecting dipyrrolobenzoquinone (+)-terreusinone.
abstract: The first synthesis of (+)-terreusinone 1, a dipyrrolobenzoquinone with a potent UV-A protecting capability, is described. Key transformations include a one-pot Larock indolization-Sonogashira coupling reaction and the hydroamination of an unsubstituted ortho-alkynylaniline catalyzed by a cationic gold(I) complex. The synthesis proceeds in eight steps from commercially available starting materials, confirming the structure and absolute configuration of the natural product.
authors.affiliation: School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
authors.forename: Christy
authors.initials: C
authors.lastname: Wang
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sperry
mesh_terms: D001230:Aspergillus / Q000737:chemistry; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D045424:Complex Mixtures / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D013473:Sunscreening Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D016227:Benzoquinones; D001688:Biological Products; D045424:Complex Mixtures; D011758:Pyrroles; D013473:Sunscreening Agents; C569912:terreusinone; D006046:Gold