132277-11-3Relevant academic research and scientific papers
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 C
Tanabe, Yoo,Seko, Shinzo,Nishii, Yoshinori,Yoshida, Taichi,Utsumi, Naoka,Suzukamo, Gohfu
, p. 2157 - 2165 (2007/10/03)
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.
A novel synthesis of α- and β-halonaphthalenes via regioselective ring cleavage of aryl(gem-dihalocyclopropyl)methanols and its application to total synthesis of lignan lactones, justicidin e and taiwanin c
Seko, Shinzo,Tanabe, Yoo,Suzukamo, Gohfu
, p. 6883 - 6886 (2007/10/02)
Acid treatment of two types of aryl(gem-dihalocyclopropyl)methanols (ADCM) 1 gave α- and β-halonaphthalenes in good yields with excellent selectivity. With the new method used as the key step, the two title natural lignan lactones were synthesized in seve
