ChemInform Abstract: Tandem Intramolecular Michael Addition/Aldol Condensation or Acylation Applied to D-Glucose-Derived Substrates: Preparation of Enantiomeric Octahydronaphthalenone Derivatives Equipped with C- and O- Functionalities.

An enantiomerically pure (1,2-isopropylidenedioxy)tetrahydrofuran derivative, 9, bearing acetonyl and propionaldehyde side chains smoothly underwent aldol cyclization under basic conditions. The major product was the cis-aldol 21S, accompanied by the trans-diasteromer 21R in a ratio of 4 to 1. Further functionalized substrates 10 and 11, with either a (4-acetyl)- or a (4-ethoxycarbonyl)-3(E)-butenyl group, smoothly underwent a tandem Michael addition/aldol condensation or acylation by treatment with sodium hydride (NaH)