Enantioselective Total Synthesis of (R,R)-Blumenol B and d9-(R,R)-Blumenol B

Shi Min Tan; Shaun W P Rees; Rebecca E Jelley; Jin Wang; Bruno Fedrizzi; David Barker

doi:10.3390/molecules27217294

Enantioselective Total Synthesis of (R,R)-Blumenol B and d₉-(R,R)-Blumenol B

Molecules. 2022 Oct 27;27(21):7294. doi: 10.3390/molecules27217294.

Authors

Shi Min Tan¹, Shaun W P Rees¹, Rebecca E Jelley¹, Jin Wang¹, Bruno Fedrizzi^{1

2}, David Barker^{1

2

3}

Affiliations

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.

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: C13-norisoprenoids; blumenol B; isotopic labelling; wine aroma.

MeSH terms

Norisoprenoids / analysis
Odorants
Stereoisomerism
Vitis*
Volatile Organic Compounds* / analysis
Wine* / analysis

Substances

Norisoprenoids
Volatile Organic Compounds

Grants and funding

This research received no external funding.