Tetrahedron

A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

M Yoshida, K Saito, Y Fujino, T Doi

Index: Yoshida, Masahito; Saito, Koya; Fujino, Yuta; Doi, Takayuki Tetrahedron, 2014 , vol. 70, # 21 p. 3452 - 3458

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Citation Number: 10

Abstract

Abstract A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu 3) efficiently induced the tandem acyl transfer- cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c).