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Synthesis 1992; 1992(11): 1112-1118
DOI: 10.1055/s-1992-26317
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Synthesis of (-)-Talaromycin A. The Use of the Δ 2 Effect for Stereocontrol at Spiroacetalic Centres

Hartmut Redlich* , Jan Bernd Lenfers, Sven Thormählen
  • *Organisch-chemisches Institut der Westfälischen Wilhelms-Universität Münster, Germany
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Publication Date:
17 September 2002 (online)

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The new concept for stereocontrol at a spiroacetalic centre in thermodynamically controlled spiroacetalization, based on the operation of the Δ2 effect, allows the synthesis of (-)-Talaromycin A {(3R,4S,6R,9R)-9-ethyl-4- hydroxy-3-hydroxymethyl-1,7-dioxaspiro[5.5]undecane} in a linear sequence from D-glucose with an overall diastereoselectivity > 97%.