Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework

Keita Komine; Kyle M Lambert; Quentin R Savage; Joshua B Cox; John L Wood

doi:10.1039/d0sc03422c

Synthetic studies toward longeracemine: a SmI₂-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework

Chem Sci. 2020 Jul 30;11(35):9488-9493. doi: 10.1039/d0sc03422c.

Authors

Keita Komine¹, Kyle M Lambert¹, Quentin R Savage¹, Joshua B Cox¹, John L Wood¹

Affiliation

¹ Department of Chemistry and Biochemistry, Baylor University One Bear Place 97348 Waco TX 76798 USA john_l_wood@baylor.edu.

Abstract

Longeracemine, a member of the Daphniphyllum family of alkaloids contains a novel carbon framework featuring a highly functionalized 2-azabicyclo[2.2.1]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-azabicyclo[2.2.1]heptadiene to a 2-azabicyclo[2.2.1]heptene that is functionally poised for conversion to the natural product.

Abstract

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