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Total Synthesis of the Fungal Metabolite Trienylfuranol A through Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions
Author(s) -
Arcile Guillaume,
Retailleau Pascal,
Ouazzani Jamal,
Betzer JeanFrancois
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100265
Subject(s) - chemistry , oxocarbenium , total synthesis , nucleophile , hydride , stereochemistry , nucleophilic addition , tetrahydrofuran , metabolite , acetaldehyde , stereoselectivity , medicinal chemistry , organic chemistry , hydrogen , catalysis , biochemistry , solvent , ethanol
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 γ‐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 obtain the desired stereochemistry. The total synthesis of trienylfuranol A was achieved in 8 steps from acetaldehyde and pyruvic acid.