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A three-step enantioselective synthesis of (+)- and (−)-α-thujone

https://doi.org/10.1039/d1ob01505b

Weeks, Kellie L. ; Williams, Jack D. ; Boyce, Gregory R. ( September 2021 , Organic & Biomolecular Chemistry)

The stereocontrolled three-step synthesis of either enantiomer of α-thujone from commercially available 3-methyl-1-butyne is described. The enantioselectivity originates from a Brown crotylation which is then conferred to the all-carbon quaternary center via chirality transfer in a gold-catalyzed cycloisomerization. The route is highly atom economical and requires no protecting groups or redox manipulations.
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Transmutation of Scent: An Evaluation of the Synthesis of Methyl Cinnamate, a Commercial Fragrance, via a Fischer Esterification for the Second-Year Organic Laboratory

https://doi.org/10.1021/acs.jchemed.0c00861

Steele, Jacob H. ; Bozor, Marie X. ; Boyce, Gregory R. ( November 2020 , Journal of Chemical Education)
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Detection of the Previously Unobserved Stereoisomers of Thujone in the Essential Oil and Consumable Products of Sage ( Salvia officinalis L.) Using Headspace Solid-Phase Microextraction–Gas Chromatography–Mass Spectrometry

https://doi.org/10.1021/acs.jafc.6b01065

Williams, Jack D. ; Yazarians, Jessica A. ; Almeyda, Chelcie C. ; Anderson, Kristin A. ; Boyce, Gregory R. ( June 2016 , Journal of Agricultural and Food Chemistry)

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