Convenient synthesis of a marine cyclopentanoid: untenone A |
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Authors: | Takahiro Kunitada Nobuo Tanaka Tsutomu Inokuchi |
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Institution: | a Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, Ridai-cho, Kita-ku, Okayama 700-0005, Japan b Department of Bioscience and Biotechnology, Faculty of Engineering, Okayama University, Tsushima-naka, Kita-ku, Okayama 700-8530, Japan |
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Abstract: | (±)-Untenone A, one of the marine cyclopentanoids, has been conveniently synthesized via (±)-cis-1-hexadecylcyclopent-2-en-1,4-diol 9 which has been produced from 1-hexadecylcyclopenta-1,3-diene 6 via photo-oxidation and the following reduction. The key step of the present synthesis is the selective alkylation of cyclopenta-1,3-diene to form 6. Optically active (−)- and (+)-untenone A have been prepared from (−)- and (+)-9, respectively, after enzymatic kinetic resolution of (±)-9. |
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