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Synlett 1995; 1995(1): 123-126
DOI: 10.1055/s-1995-4858
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Synthetic Studies Towards Milbemycin β3. Rapid Construction of a Model Spiroketal Subunit Using the Intramolecular Silyl Modified Sakurai (ISMS) Methodology

István E. Markó1 , Mark Bailey1 , Fiona Murphy1 , Jean-Paul Declercq1 , Bernard Tinant1 , Jeanine Feneau-Dupont1 , Alan Krief2 , Willy Dumont2
  • 1Département de Chimie, Université Catholique de Louvain, Place Louis Pasteur 1, B1348 Louvain-La-Neuve, Belgium
  • 2Laboratoire de Chimie Organique, Facultés Notre-Dame de la Paix, 3000 Namur, Belgium
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Publication History

Publication Date:
31 December 2000 (online)

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The ISMS condensation between allyl silane 3 and ortholactone 13 smoothly leads, after oxidative cleavage and stereoselective reduction, to spiroketal 2b, a model for the subunit present in milbemycin β3.

Milbemycin - spiroketal - ISMS condensation - allyl silane - oxonium