Synthesis of hydroxyhydrolapachol and lapachol

George Pettit, Leonard E. Houghton

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Convenient syntheses of hydroxyhydrolapachol (IIa) and lapachol (I) are reported. Treatment of 2-hydroxy-1,4-naphthoquinone with succinyl peroxide gave the carboxyethyl compound (IVa) which was esterified to give the ethyl ester (IVb). Reductive acetylation of this gave a triacetate (VI) which upon treatment with methylmagnesium iodide, and oxidation of the resulting product, gave hydroxyhydrolapachol. Repeating the reductive acetylation step with hydroxyhydrolapachol followed by treatment with iodine in xylene and saponification led to lapachol.

Original languageEnglish (US)
Pages (from-to)509-511
Number of pages3
JournalJournal of the Chemical Society C: Organic Chemistry
DOIs
StatePublished - Dec 1 1971

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this