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 substitue...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-04, Vol.23 (22), p.5224-5227
Main Authors: Tian, Guilong, Fedoseev, Pavel, Van der Eycken, Erik V.
Format: Article
Language:English
Subjects:
2-aminoimidazoles
Alkaloids - chemical synthesis
Alkaloids - chemistry
cascade reactions
Cyclization
guanidines
Guanidines - chemistry
hypervalent iodine
Iodine - chemistry
kealiinine alkaloids
Oxidation-Reduction
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Summary: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. Hypervalent iodine cascade reaction: An oxidative cascade cyclization of propargylguanidines promoted by phenyliodonium diacetate was developed, which resulted in two types of ring‐fused skeletons depending on the substitution pattern of the aromatic rings. The protocol provides an efficient route for the total synthesis of the alkaloids kealiinine B and C.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201700934