Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework |
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| Authors: | Keita Komine Kyle M Lambert Quentin R Savage Joshua B Cox John L Wood |
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| Institution: | Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco TX 76798 USA, |
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| Abstract: | Longeracemine, a member of the Daphniphyllum family of alkaloids contains a novel carbon framework featuring a highly functionalized 2-azabicyclo2.2.1]heptane core as part of an overall 5/6/5/5/6/5 skeleton. A synthetic intermediate containing the core of longeracemine has been efficiently prepared by employing a stereoselective SmI2-mediated cascade reaction to advance a 7-azabicyclo2.2.1]heptadiene to a 2-azabicyclo2.2.1]heptene that is functionally poised for conversion to the natural product.A synthetic intermediate containing the core of longeracemine, that is functionally poised for conversion to the natural product, has been efficiently prepared by employing a stereoselective SmI2-mediated cascade reaction. |
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