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Convergent Synthesis of (−)‐Quinocarcin Based on the Combination of Sonogashira Coupling and Gold(I)‐Catalyzed 6‐ endo ‐ dig Hydroamination
Author(s) -
Chiba Hiroaki,
Sakai Yuki,
Ohara Ayako,
Oishi Shinya,
Fujii Nobutaka,
Ohno Hiroaki
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300687
Subject(s) - hydroamination , sonogashira coupling , regioselectivity , alkyne , amination , intramolecular force , chemistry , pyrrolidine , convergent synthesis , stereochemistry , combinatorial chemistry , coupling reaction , stereoselectivity , catalysis , substrate (aquarium) , palladium , organic chemistry , oceanography , geology
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.