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Communication | Special issue | Vol 77, No. 1, 2009, pp.167-172
Published online, 19th May, 2008
DOI: 10.3987/COM-08-S(F)11
Enantioselective Synthesis of a 3,5,5-Trialkylated Tetronic Acid Derivative

Ken-ichi Takao,* Yuki Kojima, Tomo Miyashita, Kentaro Yashiro, Tatsuya Yamada, and Kin-ichi Tadano*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku Yokohama 223-8522, Japan

Abstract

A convenient and enantioselective method for the synthesis of 3,5,5-trialkylated tetronic acid has been developed. The Dieckmann-type condensation of enantioenriched α-acyloxy-α,α-dialkylated acetic acid ester (11) proceeded in the presence of lithium hexamethyldisilazide, providing the expected tetronic acid derivative (12) after quenching with methoxymethyl chloride. The product (12) was converted into a doubly prenylated tetronic acid derivative (13), which constitutes a substructure of perforatumone, a newly isolated polycyclic polyprenylated acylphloroglucinol-type natural product.