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Note | Regular issue | Vol 45, No. 5, 1997, pp.963-967
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7773
Model Study for the Construction of C Ring of Pimara Type Diterpenes

Takashi Fukumoto, Minoru Oguchi, Yoshinobu Kashibuchi, and Tadahiro Kato*

*Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


As the model experiment to explore the construction route of our synthetic intermediate (8), the epoxy alcohol (5) was prepared by Sharpless epoxidation including asymmetric introduction of the epoxide ring. The cyclization of 5 to the diol (6) proceeded in 40% yield by the action of Ti(OiPr)4 at room temperature. The diol (6) having more than 90% enantiomeric excess was obtained from the asymmetric epoxide (5).