Simple and efficient synthesis of highly functionalized cyclohexanes; formal total synthesis of ovalicin and fumagillin |
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Authors: | Shunya Takahashi Yayoi HongoYue Qi Ye Hiroyuki Koshino |
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Institution: | RIKEN, Wako, Saitama 351-0198, Japan |
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Abstract: | Two chiral cyclohexanes 4 and 6, which are key intermediates for the total synthesis of ovalicin 1 and fumagillin 2, respectively, were synthesized from (2R,3S) 1,2-epoxy-4-penten-3-ol. The key steps involve an efficient construction of divinylalcohol 7 using methallyl Grignard reagent 9c, and an intramolecular olefin metathesis of 7. |
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