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Synlett 1999; 1999(3): 333-335
DOI: 10.1055/s-1999-2595
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Asymmetric Biomimetic Oxidations of Phenols: Enantioselective Synthesis of (+)- and (-)-Dehydrodiconiferyl Alcohol

Petteri Rummakko* , Gösta Brunow, Marco Orlandi, Bruno Rindone
  • *Department of Chemistry, P.O. Box 55 FIN-00014 University of Helsinki, Finland; Fax (3 58)9 70 85 95 56; E-mail: Petteri.Rummakko@Helsinki.fi
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Publication Date:
31 December 1999 (online)

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Stereoselective bimolecular radical coupling reactions of phenylpropenoid phenols are described. Oppolzer's camphor sultam 1 and Evan's 2-oxazolidinone 2a-d derivatives of ferulic acid were prepared and oxidized to give dimeric benzofuran neolignan structures 11 in 40-50% overall yields. The chiral phenols were oxidized either enzymatically with hydrogen peroxide and horseradish peroxidase (HRP) or by silver oxide. The observed enantioselectivity after reductive cleavage of chiral auxiliaries gave the neolignan dehydrodiconiferyl alcohol 12 in 18-84% e.e.

asymmetric synthesis - radical - phenol coupling - chiral auxiliary