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Dearomatizing Conjugate Addition to Quinolinyl Amidines for the Synthesis of Dehaloperophoramidine through Tandem Arylation and Allylation
Author(s) -
Ishida Takayuki,
Ikota Hideo,
Kurahashi Kei,
Tsukano Chihiro,
Takemoto Yoshiji
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201305581
Subject(s) - conjugate , tandem , yield (engineering) , intramolecular force , chemistry , combinatorial chemistry , computer science , stereochemistry , engineering , mathematics , materials science , mathematical analysis , metallurgy , aerospace engineering
Dehaloperophoramidine , the dehalogenated analogue of the marine hexacyclic alkaloid perophoramidine was synthesized. The intramolecular nucleophilic dearomatizing arylation of aminoquinoline initiated by a lithium–iodine exchange and the subsequent direct allylation of the resultant azaenolate afforded a pentacyclic bisamidine compound bearing two contiguous all‐carbon quaternary centers in good yield with excellent diastereoselectivity.