Issue 17, 1996
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Novel method for the synthesis of α- and β-halogenonaphthalenes by regioselective benzannulation of aryl(gem-dihalogenocyclopropyl)methanols: application to the total synthesis of the lignan lactones, justicidin E and taiwanin C1

Yoo Tanabe,   Shinzo Seko,   Yoshinori Nishii,   Taichi Yoshida,   Naoka Utsumi  and  Gohfu Suzukamo  

Abstract

Acid treatment of two types of aryl(gem-dihalogenocyclopropyl)methanols (ADCMs) 1 and 3 gives α- and β-halogenonaphthalenes in good yields with excellent selectivity. These alternative annulations involve two distinctive types of highly regioselective acid-induced cyclopropane ring cleavage, wherein the preferential formation of more stable cationic intermediates determines the selectivity. The stereochemical mode of both the preparation and the annulation between diastereoisomers of an ADCM has been checked. As a demonstration of this annulation, a total synthesis of each of the natural lignan lactones, justicidin E 19 and taiwanin C 20, has also been performed. Since these 4-arylnaphthalenes are expected to exhibit biological activity, the anti-platelet activating factor (anti-PAF) activity of justicidin E has been assayed.

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Article information

DOI
https://doi.org/10.1039/P19960002157
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 2157-2165

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Novel method for the synthesis of α- and β-halogenonaphthalenes by regioselective benzannulation of aryl(gem-dihalogenocyclopropyl)methanols: application to the total synthesis of the lignan lactones, justicidin E and taiwanin C1

Y. Tanabe, S. Seko, Y. Nishii, T. Yoshida, N. Utsumi and G. Suzukamo, J. Chem. Soc., Perkin Trans. 1, 1996, 2157 DOI: 10.1039/P19960002157

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