Journal of natural products

Synthesis of Arieianal, a Prenylated Benzoic Acid from Piper a rieianum

SI Odejinmi, DF Wiemer

Index: Odejinmi, Sina I.; Wiemer, David F. Journal of Natural Products, 2005 , vol. 68, # 9 p. 1375 - 1379

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Citation Number: 12

Abstract

Arieianal (1) is a complex prenylated benzoic acid that was isolated from Piper arieianum. It has been synthesized through a convergent sequence that joins a functionalized diterpenoid chain to a protected aromatic core. Key steps include use of a copper enolate for selective displacement of an allylic bromide in the presence of an allylic acetate and a stereoselective Horner-Wadsworth-Emmons condensation to afford the desired E olefin of ...