Synthesis of (±) Wine Lactone and Its Analogues by a Diels–Alder Approach (Eur. J. Org. Chem. 26/2009)

Abstract

AbstractThe cover picture shows a typical panoramic scene encountered in New Zealand: a vineyard situated near Blenheim at the base of the Southern Alps. Wine lactone, a sweet‐smelling compound that contributes significantly to the aroma of a variety of white wines, is depicted in a reaction scheme in the foreground. The intramolecular Diels–Alder cycloaddition leading to wine lactone is diastereoselective, and the computationally predicted transition state is illustrated against the sky background. Scheurebe grapes and Riesling wine being poured into a glass are also depicted. Wine lactone is found in wines produced from both Scheurebe and Riesling grapes. Details are discussed in the article by M. A. Brimble et al. on p. 4405 ff.