Enantioselective total synthesis of (-)-curcuquinone via regioselective chromium-mediated benzannulation.
[reaction: see text] A short and efficient, high-yielding enantioselective total synthesis of the marine natural product (-)-curcuquinone 1 is reported involving a regioselective [3 + 2 + 1]-benzannulation reaction as the key step. Additionally, this strategy allows the isolation of curcuhydroquinone monomethyl ether 9 as an intermediate of the benzannulation reaction and its subsequent further protection toward diversified hydroquinones.
Minatti
Ana
A
Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany.
Dötz
Karl Heinz
KH
D000818:Animals; D002384:Catalysis; D002857:Chromium / Q000737:chemistry*; D003063:Cnidaria / Q000737:chemistry; D006873:Hydroquinones / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D006873:Hydroquinones; D007202:Indicators and Reagents; D012717:Sesquiterpenes; C500551:curcuquinone; D002857:Chromium