Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2.
[reaction: see text] An efficient synthetic approach to angucyclinone antibiotics, (+)-ochromycinone and (+)-rubiginone B(2), is reported. The key step involves the facile formation of 2,3-dihydrophenantren-4(1H)-one skeleton, an important framework of angucyclinone natural products, by using gold-catalyzed intramolecular [4 + 2] benzannulation reaction.
Sato
Kenichiro
K
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
Asao
Naoki
N
Yamamoto
Yoshinori
Y
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001554:Benzene / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D013237:Stereoisomerism; D000095602:Angucyclines and Angucyclinones
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D001554:Benzene; D006046:Gold; D009281:Naphthalenes; C510997:angucyclinone; C510996:rubiginone B2; D000095602:Angucyclines and Angucyclinones; C066105:rubiginones; C031721:naphthalene; C510995:ochromycinone