Enantioselective formal synthesis of (−)-aurantioclavine using Pd-catalyzed cascade cyclization and organocatalytic asymmetric aziridination

[Display omitted] •The enantioselective formal synthesis of (−)-aurantioclavine was achieved.•The core skeleton was synthesized using a Pd-catalyzed cascade cyclization.•The stereocenter was constructed by a organocatalytic asymmetric aziridination. The enantioselective formal synthesis of (−)-auran...

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Bibliographic Details
Published in:Tetrahedron letters 2018-02, Vol.59 (8), p.760-762
Main Authors: Nakano, Shun-ichi, Hamada, Yasumasa, Nemoto, Tetsuhiro
Format: Article
Language:English
Subjects:
(−)-Aurantioclavine
Cascade reaction
Indole
Organocatalysis
Palladium
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Summary:[Display omitted] •The enantioselective formal synthesis of (−)-aurantioclavine was achieved.•The core skeleton was synthesized using a Pd-catalyzed cascade cyclization.•The stereocenter was constructed by a organocatalytic asymmetric aziridination. The enantioselective formal synthesis of (−)-aurantioclavine is described. The core tricyclic skeleton was synthesized using a Pd-catalyzed Heck insertion–allylic amination cascade. The stereocenter was constructed by a highly enantioselective organocatalytic asymmetric aziridination reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.01.033