Tetrahedron

Synthesis of 6-methoxy-4H-1-benzopyran-7-ol, a character donating component of the fragrance of Wisteria sinensis

…, AP Markusse, S Vervisch, S Debenedetti, N De Kimpe

Index: Demyttenaere, Jan; Van Syngel, Kris; Peter Markusse; Vervisch, Stijn; Debenedetti, Silvia; De Kimpe, Norbert Tetrahedron, 2002 , vol. 58, # 11 p. 2163 - 2166

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Citation Number: 51

Abstract

6-Methoxy-4H-1-benzopyran-7-ol 7, a major impact flavor compound of Wisteria sinensis has been synthesized from 2, 4, 5-trimethoxybenzaldehyde 1 via scopoletin 3. The synthetic sequence comprised (i) bisdemethylation of 2, 4, 5-trimethoxybenzaldehyde 1,(ii) Wittig reaction with ethoxycarbonylmethylenetriphenylphosphor...,(iii) hydrogenation on palladium/carbon in glacial acetic acid,(iv) DIBAL-H reduction of the intermediate lactone ...