Enol ester as an olefinic partner in enyne cyclization. A novel tandem cyclization to stereodefined bicyclo[3.3.0]octenes |
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Authors: | Urabe Hirokazu Suzuki Daisuke Sasaki Misa Sato Fumie |
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Institution: | Department of Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan. hurabe@bio.titech.ac.jp |
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Abstract: | When (Z)-1-tridecen-6-ynyl propanoate was treated with a titanium(II) alkoxide reagent, Ti(O-i-Pr)4/2i-PrMgCl, a novel tandem cyclization took place to give (1RS,2RS,3SR)-3-ethyl-4-hexyl-4-bicyclo3.3.0]octene-2,3-diol virtually as a single stereoisomer after aqueous workup. The generality of this cyclization was also shown. Similarly, (Z)-3-butyl-1-tridecen-6-ynyl propanoate afforded (1RS,2RS,3SR,8SR)-8-butyl-3-ethyl-4-hexyl-4-bicyclo3.3.0]octene-2,3-diol with a diastereoselectivity of >95:5, demonstrating the simultaneous construction of a total of four consecutive stereogenic centers in the product and with virtually complete diastereoselectivity. |
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