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Paper | Special issue | Vol 99, No. 2, 2019, pp.1003-1019
Published online, 22nd November, 2018
DOI: 10.3987/COM-18-S(F)65
The Practical Synthesis of Dissymmetrical 1,3,5-Trioxazatriquinane Derivatives Comprised of Three Distinct Carbonyl Compounds

Shigeto Hirayama, Koji Obayashi, Naohisa Wada, Kousuke Ohyama, Shizuho Fuku, Koji Koyano, Fumika Karaki, Kennosuke Itoh, Hiroshi Nagase, and Hideaki Fujii*

*Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan

Abstract

We have previously synthesized various 1,3,5-trioxazatriquinane derivatives consisting of not only three identical carbonyl compounds but also two identical carbonyl moieties as well as another type of carbonyl compound. However, dissymmetrical derivatives prepared from three distinct carbonyl compounds have not yet been selectively synthesized. Herein, we developed a selective synthetic method of such dissymmetrical derivatives: free α-hydroxyaldehydes were slowly added to a solution of protected α-hydroxyaldehydes, ammonium chloride, and sodium acetate to selectively provide key intermediate oxazolines, which were successfully converted into the objective dissymmetrical derivatives.