Total synthesis of (-)-quinocarcin by gold(I)-catalyzed regioselective hydroamination.
In control: The novel and enantioselective total synthesis of (-)-quinocarcin includes the highly stereoselective preparation of the 2,5-cis-pyrrolidine by intramolecular amination, a selective substrate-controlled 6-endo-dig intramolecular alkyne hydroamination with a cationic Au(I)  catalyst, and Lewis-acid-mediated ring-opening/halogenation sequence.
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, Japan.
Hiroaki
H
Chiba
Shinya
S
Oishi
Nobutaka
N
Fujii
Hiroaki
H
Ohno
D000586:Amination; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D007546:Isoquinolines; D058116:Lewis Acids; D011759:Pyrrolidines; D006046:Gold; C038710:quinocarcin; C032519:pyrrolidine