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Updated: Aug 23, 2026

Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
Published on: August 14, 2019
Versatile asymmetric synthesis of the kavalactones: first synthesis of (+)-kavain
Thomas E Smith1, Mabel Djang, Alan J Velander
1Department of Chemistry, Williams College, Williamstown, Massachusetts 01267, USA. tsmith@williams.edu
Abstract:
[reaction: see text] Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.
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