Synthesis of (±)-myo-inositol 4-methylenephosphonate via Rh-Catalyzed hydrogenation of vinylphosphonate. (7th August 2017)

• Record Type: Journal Article
• Authors: Okauchi, Tatsuo; Nakamura, Shuya; Tsubaki, Kouta; Asakawa, Momoko; Kitamura, Mitsuru
• Is Part Of: Carbohydrate research. Volume 448(2017)
• Page Start: 24
• Page End: 27
• Publication Date: 2017-08-07
• Subjects: Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2017.05.018
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: Phosphatidylinositol phosphate (PIP) synthetase is a promising target for the development of new anti-mycobacterium compounds. We previously reported that myo -inositol 1-methylenephosphonate showed inhibitory activity against PIP synthetase. Herein, we report the synthesis of unprotected myo -inositol 4-methylenephosphonate, a constitutional isomer of myo -inositol 1-methylenephosphonate and found that the stereoselective hydrogenation of vinylphosphonate proceeded via Rh catalysis. Graphical abstract: Highlights: myo-Inositol 4-methylenephosphonate was synthesized stereoselectively. The myo-inositol derivative was isolated as a single isomer without separation. Hydrogenation of the vinylphosphonate proceeded stereoselectively using rhodium-on-carbon.