Enantioselective Total Synthesis of (<i>R,R</i>)-Blumenol B and d₉-(<i>R,R</i>)-Blumenol B

Abstract

C13-norisoprenoids are of particular importance to grapes and wines, as these molecules influence wine aroma and have been shown to significantly contribute to the distinct character of various wine varieties. Blumenol B is a putative precursor to a number of important wine aroma compounds, including the well-known compounds theaspirone and vitispirane. The enantioselective synthesis of (R,R)-blumenol B from commercially available 4-oxoisophorone was achieved using a short and easily scaleable route, which was then successfully applied to the synthesis of poly-deuterated d9-blumenol B.

Keywords

• wine aroma
• C₁₃-norisoprenoids
• blumenol B
• isotopic labelling