Total Synthesis of (+)-Conolidine by the Gold(I)-Catalyzed Cascade Cyclization of a Conjugated Enyne

A total synthesis of (+)-conolidine has been achieved via the gold­(I)-catalyzed cascade cyclization of a conjugated enyne. Remarkably, this strategy allowed for the simultaneous formation of the indole ring and the ethylidene-substituted piperidine moiety of (+)-conolidine under homogeneous gold ca...

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Veröffentlicht in:Journal of organic chemistry 2016-07, Vol.81 (13), p.5690-5698
Hauptverfasser: Naoe, Saori, Yoshida, Yusuke, Oishi, Shinya, Fujii, Nobutaka, Ohno, Hiroaki
Format: Artikel
Sprache:eng
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Zusammenfassung:A total synthesis of (+)-conolidine has been achieved via the gold­(I)-catalyzed cascade cyclization of a conjugated enyne. Remarkably, this strategy allowed for the simultaneous formation of the indole ring and the ethylidene-substituted piperidine moiety of (+)-conolidine under homogeneous gold catalysis in an enantioselective manner (88–91% ee).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00720