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Communication | Regular issue | Vol 36, No. 9, 1993, pp.1957-1960
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6415
Total Synthesis of (±)-Cembranolide via Cr(II) Mediated Intramolecular Macrocyclization of β-Alkoxycarbonylallyl Halide

Kiyoshi Nishitani, Toshihiko Konomi, Youji Mimaki, Takashi Tsunoda, and Koji Yamakawa*

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

Abstract

The ω-formyl-β-methoxycarbonylallyl halide (20), prepared from geraniol and methyl β-hydroxypropionate, was cyclized efficiently and with high stereoselectivity to 14-membered cis-cycloalkenol (21) by CrCl2 in DMF. The cycloalkenol was treated with p-TsOH to give an excellent yield of (±)-cis-cembranolide (IV).