Asymmetric total synthesis of nigerone.
[reaction: see text] An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone is reported. The key step was an eight-step isomerization process to form the final natural product. The isomerization precursor was constructed via asymmetric oxidative biaryl coupling of an advanced intermediate with a 1,5-diaza-cis-decalin copper catalyst.
Divirgilio
Evan S
ES
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
Dugan
Elizabeth C
EC
Mulrooney
Carol A
CA
Kozlowski
Marisa C
MC
D001688:Biological Products / Q000138:chemical synthesis*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry; D007536:Isomerism; D008956:Models, Chemical; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry
C430116:1,5-diazadecalin; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D006574:Heterocyclic Compounds, 2-Ring; D009281:Naphthalenes; D010880:Piperidines; D011753:Pyrones; C432445:naphthopyrone dimer; C518566:nigerone; D003300:Copper