Dearomatizing Conjugate Addition to Quinolinyl Amidines for the Synthesis of Dehaloperophoramidine through Tandem Arylation and Allylation1. Issue 39 (9th August 2013)

• Record Type: Journal Article
• Authors: Ishida, Takayuki; Ikota, Hideo; Kurahashi, Kei; Tsukano, Chihiro; Takemoto, Yoshiji
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 39(2013)
• Page Start: 10204
• Page End: 10207
• Publication Date: 2013-08-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201305581
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>Dehaloperophoramidine</bold>, 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.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg3h9k5d17" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>