1402461-15-7Relevant articles and documents
Convergent synthesis of (-)-quinocarcin based on the combination of sonogashira coupling and gold(I)-catalyzed 6-endo-dig hydroamination
Chiba, Hiroaki,Sakai, Yuki,Ohara, Ayako,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
, p. 8875 - 8883 (2013/07/26)
The total synthesis of the pentacyclic tetrahydroisoquinoline alkaloid quinocarcin, which possesses intriguing structural and biological features, has been achieved through a gold(I)-catalyzed regioselective hydroamination reaction. It is noteworthy that the regioselectivity of the intramolecular hydroamination of an unsymmetrical alkyne could be completely switched through substrate control. Other key features of this synthesis include the highly stereoselective synthesis of 2,5-cis-pyrrolidine through the intramolecular amination of the bromoallene and the Lewis acid mediated ring opening of dihydrobenzofuran. Golden(I): A convergent asymmetric total synthesis of quinocarcin employed Sonogashira and Au-catalyzed hydroamination reactions (see scheme). The regioselectivity of the intramolecular hydroamination of an unsymmetrical alkyne was switched by substrate control. Copyright
