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Paper | Special issue | Vol 47, No. 1, 1998, pp.263-270
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)10
An Applied Stereocontrolled Synthesis of Piperidine Derivative Utilizing Diastereo- selective Reaction of Chiral 1,3-Oxazolidine with Grignard Reagent; Asymmetric Synthesis of an Alkaloid, (-)-Sedamine

Hadi Poerwono, Kimio Higashiyama,* and Hiroshi Takahashi

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

A facile total synthesis of enantiomerically pure (-)-sedamine, known as a naturally occurring alkaloid, was accomplished by use of the diastereoselective addition of Grignard reagent to a chiral 1,3-oxazolidine, and utilizing of 1-aza-4-oxabicyclo[4.3.0]nonane derivative as a key intermediate. A diastereomeric pair, (-)-allosedamine, was also recovered as a minor product.