Enantioselective Total Synthesis of (R,R)-Blumenol B and d9-(R,R)-Blumenol B |
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| Authors: | Shi Min Tan Shaun W. P. Rees Rebecca E. Jelley Jin Wang Bruno Fedrizzi David Barker |
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| Affiliation: | 1.School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland 1010, New Zealand;2.Centre for Green Chemical Science, School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland 1010, New Zealand;3.MacDiarmid Institute for Advanced Materials and Nanotechnology, Victoria University of Wellington, Wellington 6012, New Zealand |
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| 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. |
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| Keywords: | wine aroma C13-norisoprenoids blumenol B isotopic labelling |
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