Versatile asymmetric synthesis of the kavalactones: first synthesis of (+)-kavain

Organic Letters
Thomas E SmithSophie Van Alphen

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.

References

Dec 24, 1976·The Journal of Organic Chemistry·Z H Israili, E E Smissman
Jul 1, 1990·Clinical and Experimental Pharmacology & Physiology·D D Jamieson, P H Duffield
Jan 22, 1998·Planta medica·U SeitzJ Gleitz
Oct 17, 1998·Planta medica·G Boonen, H Häberlein
Nov 26, 1998·Progress in Neuro-psychopharmacology & Biological Psychiatry·S S BaumH Rommelspacher
Feb 1, 2000·Journal of Clinical Psychopharmacology·M H Pittler, E Ernst
Jan 17, 2002·Journal of the American Chemical Society·David A EvansC Wade Downey
Apr 2, 2002·Organic Letters·David A EvansJason S Tedrow
Apr 2, 2002·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·D WuR S Ramsewak
Jun 25, 2003·Journal of Hepatology·Felix StickelDetlef Schuppan
Nov 4, 1950·Nature·D KOSTERMANS

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Citations

Aug 9, 2011·Bioscience, Biotechnology, and Biochemistry·Arata Yajima
Sep 16, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tran Dang Xuan, Rolf Teschke
Dec 18, 2012·Evidence-based Complementary and Alternative Medicine : ECAM·Tan Eng-ChongRohana Yusof
Jun 20, 2008·Journal of Separation Science·Roberto CirilliFrancesco La Torre
Feb 6, 2021·Angewandte Chemie·Chang-Yun ShiLiang Yin
May 9, 2008·Organic Letters·Rodolfo Tello-Aburto, Horacio F Olivo
Jul 1, 2021·Organic & Biomolecular Chemistry·James I BowenChristine L Willis
Sep 19, 2012·The Journal of Organic Chemistry·Jessica BaigetMercè Font-Bardia
Sep 24, 2014·Organic Letters·Justine N deGruyter, William A Maio
Dec 2, 2011·Organic Letters·Esdrey Rodriguez-CárdenasHoracio F Olivo
Jun 6, 2013·The Journal of Organic Chemistry·Masahiro MinenoHideya Mizufune
Jan 7, 2020·ACS Chemical Neuroscience·Andrey VolginAllan Kalueff

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