title: Two approaches to the aromatic core of the aminonaphthoquinone antibiotics.
abstract: Two complementary approaches are presented for the synthesis of the quinone chromophores of the naphthoquinone ansamycins and related natural products. The first involves the use of an improved protocol for the manganese(III) acetate mediated cyclization of 5-aryl-1,3-dicarbonyl compounds to β-naphthols, leading to the simple, scalable preparation of building blocks suitable for the synthesis of naturally occurring aminonaphthoquinones. The second approach involves the Diels-Alder reaction of a series of new, ester-containing Danishefsky-type dienes with N-protected aminobenzoquinones to allow more expeditious access to similar intermediates.
authors: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
authors: Christopher C
authors: CC
authors: Nawrat
authors: Leoni I
authors: LI
authors: Palmer
authors: Alexander J
authors: AJ
authors: Blake
authors: Christopher J
authors: CJ
authors: Moody
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C400575:3-aminonaphthoquinone; D000900:Anti-Bacterial Agents; D009285:Naphthoquinones