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Paper | Regular issue | Vol 32, No. 5, 1991, pp.923-936
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5682
First Synthesis of (+)-Septorine

Akihiro Ohta,* Akihiko Kojima, Terumi Saito, Kayoko Kobayashi, Hideo Saito, Koichi Wakabayashi, Susumu Honma, Chiseko Sakuma, and Yutaka Aoyagi

*Tokyo College of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

(+)-Septorine, a metabolite of Septoria nodorum, was synthesized via alanyl-isoleucyl anhydride (2) from L-isoleucine at the first time. Compound (2) was led to a pyrazine-carboxaldehyde (13), which was treated with p-methoxymethoxyphenylmagnesium bromide to afford an alcohol (14) in a quantative yield. The alcohol (14) was oxidized to ketone (16), which was subjected to the Pummerer reacton and the following hydrolysis to give (+)-septorine.