• Medientyp: E-Artikel
  • Titel: A Chemoenzymatic Approach to the Stereocontrolled Synthesis of the C1–C11 fragment of (+)‐Peloruside A
  • Beteiligte: Schönherr, Heike; Mollitor, Jan; Schneider, Christoph
  • Erschienen: Wiley, 2010
  • Erschienen in: European Journal of Organic Chemistry
  • Sprache: Englisch
  • DOI: 10.1002/ejoc.201000369
  • ISSN: 1434-193X; 1099-0690
  • Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
  • Entstehung:
  • Anmerkungen:
  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>A highly efficient and diastereoselective synthesis of the C1–C11 fragment of the marine natural product (+)‐peloruside A has been developed. Through enzymatic desymmetrization of diethyl 3‐hydroxyglutarate with lipase B from <jats:italic>Candida antarctica</jats:italic> a large‐scale access to enantiomerically highlyenriched starting material was achieved. Subsequent stereogenerating key steps utilized in the synthesis were a Sharpless asymmetric dihydroxylation and a doubly diastereoselective Mukaiyama aldol reaction to set up thestereogenic centers at C2, C3, C5, C7 and C8 with correct absolute configuration.</jats:p>