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

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...

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Detalles Bibliográficos
Autores principales: Komine, Keita, Lambert, Kyle M., Savage, Quentin R., Cox, Joshua B., Wood, John L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162136/
https://www.ncbi.nlm.nih.gov/pubmed/34094215
http://dx.doi.org/10.1039/d0sc03422c
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author Komine, Keita
Lambert, Kyle M.
Savage, Quentin R.
Cox, Joshua B.
Wood, John L.
author_facet Komine, Keita
Lambert, Kyle M.
Savage, Quentin R.
Cox, Joshua B.
Wood, John L.
author_sort Komine, Keita
collection PubMed
description 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 SmI(2)-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.
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spelling pubmed-81621362021-06-04 Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework Komine, Keita Lambert, Kyle M. Savage, Quentin R. Cox, Joshua B. Wood, John L. Chem Sci Chemistry 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 SmI(2)-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. The Royal Society of Chemistry 2020-07-30 /pmc/articles/PMC8162136/ /pubmed/34094215 http://dx.doi.org/10.1039/d0sc03422c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Komine, Keita
Lambert, Kyle M.
Savage, Quentin R.
Cox, Joshua B.
Wood, John L.
Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
title Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
title_full Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
title_fullStr Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
title_full_unstemmed Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
title_short Synthetic studies toward longeracemine: a SmI(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
title_sort synthetic studies toward longeracemine: a smi(2)-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162136/
https://www.ncbi.nlm.nih.gov/pubmed/34094215
http://dx.doi.org/10.1039/d0sc03422c
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