A concise route to the C2-symmetric tricyclic skeleton of ryanodine |
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| Authors: | Koji Hagiwara Masafumi Himuro Masayuki Inoue |
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| Institution: | a Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
b Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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| Abstract: | Ryanodine is a potent calcium channel modulator. In this Letter, we report the 10-step synthesis of the highly substituted tricyclic ring system of ryanodine. Diels-Alder reaction via dearomatization of 2,5-dimethylbenzene-1,4-diol and subsequent SmI2-mediated reductive coupling of eight-membered 1,5-diketone efficiently introduced the four consecutive fully substituted carbons of the tricyclo3.3.2.02,6]decane system. |
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| Keywords: | Ryanodine Dearomatization Diels-Alder reaction Ring expansion Transannular cyclization Samarium iodide |
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