title: Toward an asymmetric synthesis of the dimeric pyranonaphthoquinone antibiotic crisamicin A.
abstract: A full account of our efforts toward an asymmetric synthesis of crisamicin A are presented. The key steps include a Hauser-Kraus annulation of a cyanophthalide with a chiral enone-lactone, a stereoselective cyclization-reduction to install the pyran unit, and a Suzuki homocoupling to forge the key biaryl bond. This work has culminated in the asymmetric synthesis of a dimer bearing the complete carbon skeleton of the dimeric pyranonaphthoquinone natural product crisamicin A.
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland 1010, New Zealand.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
authors.forename: Najmah P S
authors.initials: NP
authors.lastname: Hassan
authors.forename: Briar J
authors.initials: BJ
authors.lastname: Naysmith
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sperry
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D007783:Lactones; D009285:Naphthoquinones; D011714:Pyrans; C048652:crisamicin A