Synthesis of 6,6-dimethyltricyclo[5.4.0.02,8]undecane-2,9-diol for (ent-)longipinane-type sesquiterpenoids using two types of radical cyclization reactions |
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Authors: | Kazuma Matsunaga Kazuhiko Takatori Hiroshi Kogen Naoki Saito |
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Institution: | Meiji Pharmaceutical University, Noshio, Kiyose, Tokyo 204-8588, Japan |
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Abstract: | A synthetic route to 6,6-dimethyltricyclo5.4.0.02,8]undecane-2,9-diol, a key precursor to (ent-)longipinane-type sesquiterpenoids, is described. This unique core common to (ent-)longipinanes was constructed using two types of intramolecular radical cyclization reactions, namely, intramolecular coupling of an acid chloride and an alkyl iodide mediated by SmI2, TBAI and HMPA, and the coupling of a ketone and an epoxide mediated by Cp2TiI2 and SmI2. |
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Keywords: | Radical cyclization Longipinane Ireland-Claisen rearrangement |
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