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Synlett 2001; 2001(11): 1796-1798
DOI: 10.1055/s-2001-18088
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Asymmetric Synthesis of S-(+)-Argentilactone and S-(-)-Goniothalamin

Andreas Job* , Michael Wolberg, Michael Müller, Dieter Enders
  • *Institut für Organische Chemie, RWTH Aachen, Professor-Pirlet-Straße 1, 52074 Aachen, Germany; Fax + 49(241)8 88 81 27; E-mail: enders@rwth-aachen.de
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Publication Date:
29 October 2001 (online)

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The asymmetric synthesis of an α,β-unsaturated δ-lactone equivalent 8 as a key intermediate towards the total synthesis of a variety of natural products bearing such structural motifs is reported. An enzymatic approach was applied to provide both enantiomers of compound 8 using recLBADH (ee > 99%) and baker's yeast (ee = 94%), respectively. The utility of the intermediate was demonstrated by the total synthesis of the non-natural enantiomers of argentilactone [(S)-1] and goniothalamin [(S)-2].

natural products - enzymes - asymmetric synthesis - Wittig reactions - lactones