TY - JOUR
T1 - Synthesis of hydroxyhydrolapachol and lapachol
AU - Pettit, George
AU - Houghton, Leonard E.
PY - 1971/12/1
Y1 - 1971/12/1
N2 - 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.
AB - 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.
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U2 - 10.1039/J39710000509
DO - 10.1039/J39710000509
M3 - Article
AN - SCOPUS:37049125168
SN - 0022-4952
SP - 509
EP - 511
JO - Journal of the Chemical Society C: Organic Chemistry
JF - Journal of the Chemical Society C: Organic Chemistry
ER -