Biomimetic synthesis of antimalarial naphthoquinones.
The total synthesis of naphthoquinone natural products isolated from the Bignoniaceae plant family is described. Pinnatal, isopinnatal, sterekunthals A and B, pyranokunthones A and B, and anthrakunthone have been prepared along the lines of a biosynthetic proposal involving pericyclic reactions as key steps. The first case of catalysis in oxa 6pi electrocyclizations is reported.
Malerich
Jeremiah P
JP
Department of Chemistry, University of California-Berkeley, Berkeley, California 94720-1460, USA.
Maimone
Thomas J
TJ
Elliott
Gregory I
GI
Trauner
Dirk
D
D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D029402:Bignoniaceae / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D000962:Antimalarials; D009285:Naphthoquinones; D010936:Plant Extracts