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

Tian Guilong | Zendy; Fedoseev Pavel | Zendy; Van der Eycken Erik V. | Zendy

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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

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.

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