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

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.

SUBMITTER: Komine K

PROVIDER: S-EPMC8162136 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Komine Keita K Lambert Kyle M KM Savage Quentin R QR Cox Joshua B JB Wood John L JL

Chemical science 20200730 35

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 t ...[more]

PMID: 34094215

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