Synthesis

New Syntheses of the Benzoquinone Primin and its Water-Soluble Analog Primin Acid via Heck Reactions

S Mabic, L Vaysse, C Benezra, JP Lepoittevin

Index: Mabic; Vaysse; Benezra; Lepoittevin Synthesis, 1999 , # 7 p. 1127 - 1134

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Citation Number: 11

Abstract

Abstract: The syntheses of primin, 2-methoxy-6-pentylbenzoquinone (1), a major allergen of Primula obconica, and its watersoluble acid analog primin acid (2) are reported. The key steps were ortho-lithiation reactions of protected hydroquinones, palladium coupling (Heck) reactions, and salcomine-catalyzed oxidations of phenols to quinones. Key words: primin, quinone, ortho-lithiation, palladium coupling, salcomine

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