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- Title
Convergent Synthesis of (−)-Quinocarcin Based on the Combination of Sonogashira Coupling and Gold(I)-Catalyzed 6- endo- dig Hydroamination.
- Authors
Chiba, Hiroaki; Sakai, Yuki; Ohara, Ayako; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki
- Abstract
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.
- Subjects
SONOGASHIRA reaction; HYDROAMINATION; TETRAHYDROISOQUINOLINES; ALKYNES; CLINICAL trials
- Publication
Chemistry - A European Journal, 2013, Vol 19, Issue 27, p8875
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201300687