Total synthesis of antofine using the net [5+5]-cycloaddition of gamma,delta-unsaturated carbene complexes and 2-alkynylphenyl ketones as a key step.
A compound containing all of the carbons of the anticancer agent antofine was produced in a single step from the coupling of a gamma,delta-unsaturated carbene complex with a 2-alkynylphenyl ketone derivative. Subsequent conversion to antofine was effected in three steps.
Camacho-Davila
Alejandro
A
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
Herndon
James W
JW
D006838:Hydrocarbons / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010618:Phenanthrolines / Q000737:chemistry*
D006838:Hydrocarbons; D007211:Indoles; D007659:Ketones; D010618:Phenanthrolines; C473343:antofine; C030011:carbene; D008697:Methane