Synthesis of β-Lapachone

  • Author: Veronika Belusa
  • Published Date: 20 October 2014
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Synthesis of β-Lapachone

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The biologically active naphthoquinones lapachol, α-lapachone, and β-lapachone (pictured) were originally isolated from the bark of the lapacho tree (Tabebuia sp.). These natural products show a wide range of biological activities such as antitumor, antibacterial, antiplasmodial, antiangiogenic, trypanocidal, and anti-inflammatory responses.


Tadashi Katoh and colleagues, Tohoku Pharmaceutical University, Sendai, Japan, have synthesized β-lapachone in 70 % overall yield in four steps. The synthesis starts from commercially available 1,4-naphthoquinone. The key step of the synthesis is a cyclization/hydration/oxidation cascade reaction of 2-prenyl-1,4-naphthoquinone leading to target β-lapachone in one step. Advantages to previously reported methods are a higher overall yield, easier operation, and a less expensive starting material.


 

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Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH