Stereoselective synthesis of (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid via C-H insertion of alkylidenecarbene.

Ohira, Susumu; Akiyama, Megumi; Kamihara, Kumiko; Isoda, Yuichi; Kuboki, Atsuhito.

The aminocyclitol moiety of (+)-trehazolin, a powerful trehalase inhibitor, was synthesized in a stereocontrolled manner from cis-2-butene-1,4-diol via C-H insertion reaction of the alkylidenecarbene, followed by regioselective opening of the epoxide ring. It was obtained in an enantiomerically pure form by twice using Sharpless asym. epoxidation.

Bioscience, Biotechnology, and Biochemistry

Japan Society for Bioscience, Biotechnology, and Agrochemistry

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