Synthesis of hydroxyhydrolapachol and lapachol

George Pettit, Leonard E. Houghton

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 - 1971

Fingerprint

lapachol
Acetylation
Saponification
Xylenes
Peroxides
Iodides
Iodine
Esters
Oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of hydroxyhydrolapachol and lapachol. / Pettit, George; Houghton, Leonard E.

In: Journal of the Chemical Society C: Organic Chemistry, 1971, p. 509-511.

Research output: Contribution to journalArticle

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