143264-72-6Relevant academic research and scientific papers
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
Remote chiral induction in vinyl sulfonium salt-mediated ring expansion of hemiaminals into epoxide-fused azepines
Yar, Muhammad,Unthank, Matthew G.,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
, p. 372 - 375 (2011/10/09)
The planet of the azepines: Epoxy-fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four- or five-position of the hemiaminal. The key step involves ring-opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur ylide. Copyright
The synthesis of 4'-t-butylcarbamyl- and 4'-p-toluenesulphonamidyl-2',3'- dideoxy pyrimidine nucleoside analogues
Pickering,Malhi,Coe,Walker
, p. 1493 - 1506 (2007/10/02)
The preparation of 4'-t-butylcarbamyl-2',3'-dideoxy thymidine, uridine and 5-ethyl uridine nucleoside analogues and 4'-p-toluenesulphonamidyl-2',3'- dideoxy thymidine and 5-ethyl uridine nucleoside analogues from L- pyroglutamic acid is reported.
