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Synthesis of β‐Lapachone, a Potential Anticancer Agent from the Lapacho Tree
Author(s) -
Katoh Takeru,
Monma Hiromitsu,
Wakasugi Jun,
Narita Koichi,
Katoh Tadashi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403064
Subject(s) - chemistry , naphthoquinone , prenylation , natural product , yield (engineering) , combinatorial chemistry , cascade , total synthesis , stereochemistry , organic chemistry , chromatography , materials science , metallurgy , enzyme
A pharmaceutically important natural product, β‐lapachone, was efficiently synthesized in four steps in 70 % overall yield starting from commercially available 1,4‐naphthoquinone. The key step of the synthesis was the direct conversion of 2‐prenyl‐1,4‐naphthoquinone into β‐lapachone through an advantageous cyclization/hydration/oxidation cascade process.