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Total Synthesis of the fungal metabolite Trienylfuranol A via Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions

Abstract : Herein, we describe the first total synthesis of trienylfuranol A, a fungal triene-substituted tetrahydrofuran metabolite. The stereoselectivity of the chiral center bearing the trienyl side chain was diastereodivergently controlled by the addition of nucleophilic species on substituted gamma-butyrolactone. Remarkably, the C-nucleophilic species or hydride addition onto oxocarbenium intermediate leads to the opposite diastereoselectivity reported for Kishi or Woerpel models. The use of Hantzsch ester (HEH) as organic hydride donor has enabled us to access to the desired stereochemistry. The total synthesis of trienylfuranol A was achieved in 8 steps from acetaldehyde and pyruvic acid.
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https://hal-universite-paris-saclay.archives-ouvertes.fr/hal-03215484
Contributor : Jean-Francois Betzer Connect in order to contact the contributor
Submitted on : Monday, May 3, 2021 - 1:13:50 PM
Last modification on : Saturday, July 3, 2021 - 12:25:21 AM
Long-term archiving on: : Wednesday, August 4, 2021 - 7:04:03 PM

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Guillaume Arcile, Pascal Retailleau, Jamal Ouazzani, Jean-François Betzer. Total Synthesis of the fungal metabolite Trienylfuranol A via Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2021, 2021 (13), pp.2050-2054. ⟨10.1002/ejoc.202100265⟩. ⟨hal-03215484⟩

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