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Hypervalent Iodine(III)‐Mediated Cascade Cyclization of Propargylguanidines and Total Syntheses of Kealiinine B and C
Author(s) -
Tian Guilong,
Fedoseev Pavel,
Van der Eycken Erik V.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700934
Subject(s) - hypervalent molecule , chemistry , cascade , substituent , iodine , acetylene , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , chromatography
Abstract 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.