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Molecules 2016, 21(8), 988; doi:10.3390/molecules21080988

Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone

1
Chaire ABI—AgroParisTech, CEBB, 3 rue des Rouges Terres, 51110 Pomacle, France
2
Institut Jean-Pierre Bourgin, INRA, AgroParisTech, CNRS, Université Paris-Saclay, RD10, 78026 Versailles Cedex, France
3
Circa Group Pty Ltd., 34 Norkfolk Court, Coburg, 3058 Victoria, Australia
4
School of Science and Technology, University of New England, Armidale, 2350 New South Wales, Australia
5
UMR 782 GMPA, INRA, AgroParisTech, CNRS, Université Paris-Saclay, Avenue Lucien Brétignières, 78850 Thiverval-Grignon, France
*
Authors to whom correspondence should be addressed.
Academic Editor: Christophe Len
Received: 28 June 2016 / Revised: 21 July 2016 / Accepted: 23 July 2016 / Published: 29 July 2016
View Full-Text   |   Download PDF [1687 KB, uploaded 29 July 2016]   |  

Abstract

Chiral epoxides—such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)—are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to moderate overall yield (20%–50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite ((eco)toxic) and borane (carcinogen). Herein, starting from levoglucosenone (LGO), a biobased chiral compound obtained through the flash pyrolysis of acidified cellulose, we propose a safer and more sustainable chemo-enzymatic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps. This route afforded ethyl and methyl (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, respectively. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO. View Full-Text
Keywords: epoxide; flavor; levoglucosenone; chirality; total synthesis epoxide; flavor; levoglucosenone; chirality; total synthesis
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MDPI and ACS Style

Peru, A.A.M.; Flourat, A.L.; Gunawan, C.; Raverty, W.; Jevric, M.; Greatrex, B.W.; Allais, F. Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone. Molecules 2016, 21, 988.

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