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Communication | Special issue | Vol 86, No. 2, 2012, pp.985-989
Published online, 28th August, 2012
DOI: 10.3987/COM-12-S(N)104
A NEW ENTRY TO THE SYNTHESIS OF PRIMIN VIA A B-ALKYL SUZUKI–MIYAURA CROSS-COUPLING REACTION

Kazuhiro Watanabe, Tomohiro Sugizaki, Yumi Tozawa, and Tadashi Katoh*

*Laboratory of Synthetic and Medicinal Chemistry, Department of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Primin, a biologically active benzoquinone natural product, was efficiently synthesized in 57% overall yield in six steps starting from commercially available 5-iodovanillin. The synthetic method involves crucial steps, including a B-alkyl Suzuki–Miyaura cross-coupling reaction to directly install an alkyl side chain in an aromatic ring and elaboration of quinone functionality by degradative oxidation using Fremys salt to yield the target primin.