合成路线:Oxidative cleavage of methylindene (I) by means of Na2Cr2O7 produces 2-acetylphenylacetic acid (II).Fischer esterification of keto acid (II) gives keto ester (III),which is subjected to intramolecular Claisen condensation and air oxidation,yielding the hydroxy naphthoquinone (IV) (1).Alkylation of (IV) with prenyl bromide (V) leads to a mixture of lapachol (VII) and minor amounts of the prenyl ether isomer (VI) (1-3).Finally,cyclization of (VII) in concentrated H2SO4 gives rise to the target compound.
参考文献标题:Synthesis of beta-lapachone and its intermediates
文献作者:Jiang,Z.; Hogeland,J.(Dana-Farber Cancer Institute)
参考来源:WO 0259103
合成路线:Oxidative cleavage of methylindene (I) by means of Na2Cr2O7 produces 2-acetylphenylacetic acid (II).Fischer esterification of keto acid (II) gives keto ester (III),which is subjected to intramolecular Claisen condensation and air oxidation,yielding the hydroxy naphthoquinone (IV) (1).Alkylation of (IV) with prenyl bromide (V) leads to a mixture of lapachol (VII) and minor amounts of the prenyl ether isomer (VI) (1-3).Finally,cyclization of (VII) in concentrated H2SO4 gives rise to the target compound.
参考文献标题:beta-Lapachone: Synthesis of derivatives and activities in tumor models
文献作者:Schaffner-Sabba,K.; Schmidt-Ruppin,K.H..; Wehrli,W.; Schuerch,A.R.; Wasley,J.W.F.
参考来源:J Med Chem 1984,27(8),990
合成路线:Oxidative cleavage of methylindene (I) by means of Na2Cr2O7 produces 2-acetylphenylacetic acid (II).Fischer esterification of keto acid (II) gives keto ester (III),which is subjected to intramolecular Claisen condensation and air oxidation,yielding the hydroxy naphthoquinone (IV) (1).Alkylation of (IV) with prenyl bromide (V) leads to a mixture of lapachol (VII) and minor amounts of the prenyl ether isomer (VI) (1-3).Finally,cyclization of (VII) in concentrated H2SO4 gives rise to the target compound.
参考文献标题:A preparative synthesis of lapachol and related naphthoquinones
文献作者:Sun,J.S.; Geiser,A.H.; Frydman,B.
参考来源:Tetrahedron Lett 1998,398221
合成路线:Esterification of 1-naphthol (I) with 3-methylcrotonic acid chloride (II) provides ester (III),which subsequently rearranges to the hydroxy ketone (IV).Cyclization of (IV) under acidic conditions provides the tricyclic system (V).Keto group reduction in (V) by means of LiAlH4 leads to alcohol (VI),which upon acidic treatment is dehydrated to olefin (VII).Further catalytic hydrogenation of (VII) in the presence of Pd/C yields the dihydro naphthopyran (VIII).Electrophilic nitration of (VIII) provides (IX).After reduction of nitro derivative (IX) to the corresponding amine (X) by means of Sn/HCl,acylation with acetic anhydride furnishes acetamide (XI).Finally,oxidation of (XI) with concentrated nitric acid gives rise to the target ortho-quinone .
参考文献标题:The total synthesis of beta-lapachone
文献作者:Amaral,A.C.F.; Barnes,R.A.
参考来源:J Heterocycl Chem 1992,291457
产品链接: CAS No. 4707-32-8››