Hypervalent Iodine(III)-Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C

An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate (PIDA) was developed. The protocol provides an efficient route for the synthesis of the alkaloids kealiinines B and C as well as homologues. The difference in the electronic nature of the acetylene substituent resulted in two ways of the cyclization. A plausible mechanism is proposed based on the experimental results. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Authors
Tian G.1 , Fedoseev P.1 , Van Der Eycken E.V.
Journal
Chemistry - A European Journal
Publisher
Wiley-VCH Verlag
Number of issue
22
Language
English
Pages
5224-5227
Status
Published
Link
External link
DOI
10.1002/chem.201700934
Volume
23
Year
2017
Organizations
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 2 Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya street, Moscow, 117198, Russian Federation
Keywords
2-aminoimidazoles; cascade reactions; guanidines; hypervalent iodine; kealiinine alkaloids
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/5948/
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