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Title: Construction of the Pyrrolo[2,3- d]carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide
Authors: Matsuoka, Junpei
Kumagai, Hiroshi
Inuki, Shinsuke
Oishi, Shinya
Ohno, Hiroaki
Author's alias: 松岡, 純平
井貫, 晋輔
大石, 真也
大野, 浩章
Issue Date: 19-Jul-2019
Publisher: American Chemical Society
Journal title: Journal of Organic Chemistry
Volume: 84
Issue: 14
Start page: 9358
End page: 9363
Abstract: We achieved direct construction of the common pyrrolo[2, 3-d]carbazole core of aspidosperma and malagasy alkaloids by a gold-catalyzed cascade cyclization of ynamide. This reaction involves intramolecular cyclization from indole to ynamide followed by trapping of the resulting iminium intermediate. Through the use of chiral gold complexes, an enantiomerically enriched pyrrolo[2, 3-d]carbazole was obtained in up to 74% ee. This methodology was successfully applied to the asymmetric formal synthesis of vindorosine.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
The full-text file will be made open to the public on 3 June 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1021/acs.joc.9b01149
PubMed ID: 31244165
Appears in Collections:Journal Articles

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