Issue 37, 2021

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
31 iyl 2021
Accepted
26 avq 2021
First published
26 avq 2021

Org. Biomol. Chem., 2021,19, 8018-8020

Author version available

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

K. L. Weeks, J. D. Williams and G. R. Boyce, Org. Biomol. Chem., 2021, 19, 8018 DOI: 10.1039/D1OB01505B

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