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Communication | Special issue | Vol 39, No. 1, 1994, pp.43-46
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)26
Total Synthesis of (±)-Diplophyllin Using Intramolecular Cyclization of ω-Formyl-β-alkoxycarbonylallysilane

Kiyoshi Nishitani, Jun Suzuki, Hideyasu Ishibashi, Yoshiko Saitoh, Shoko Kariya, and Koji Yamakawa*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan


ω-Formyl-β-ethoxycarbonylallylsilane derivative (15) was prepared from methyloctalone in several steps. Intramolecular cyclization of the allylsilane (15) was effected by BF3-OEt2 to give hydroxy esters (17 and 18) in good stereoselectivity at C-7. The hydroxy ester (17) was converted into (±)-diplophyllin (I) with p-TsOH in an excellent yield.