Trimethyl orthoacetate can be used as an alternative to CH2N2 on the methylation of β-OH groups of (poly)hydroxynaphthazarins. In contrast to CH2N2 it can be applied both to complete and to selective methylation of these groups.
GlazunovV.P., TchizhovaAYa, ShestakO.P., SopelnyakG.I., AnufrievVPh. (2001) Chemistry of naphthazarin derivatives. Determination of structures of substituted 2-hydroxy-6(7)-methoxynaphthazarins and 7(8)-hydroxypyranonaphthazarins by IR spectroscopy. Russian Chemical Bulletin, International Edition, 50, 95–100.
3.
GlazunovV.P., YakubovskayaAYa, PokhiloN.D., BochinskayaN.V., AnufrievVPh. (2003) Chemistry of naphthazarin derivatives. Direct observation of prototropic tautomerism of (poly)hydroxynaphthazarins by IR spectroscopy. Russian Chemical Bulletin, International Edition, 52, 198–207.
4.
NicolaouK.C., GrayD.L.F. (2004) Total synthesis of hybocarpone and analogues thereof. A facile dimerization of naphthazarins to pentacyclic systems. Journal of the American Chemical Society, 126, 607–612.
5.
PokhiloN.D., ShuvalovaM.I., LebedkoM.V., SopelnyakG.I., YakubovskayaAYa, MishchenkoN.P., FedoreyevS.A., AnufrievVPh. (2006) Synthesis of echinamines A and B, the first aminated hydroxynaphthazarins produced by the sea urchin Scaphechinus mirabilis, and its analogues. Journal of Natural Products, 69, 1125–1129.
6.
PokhiloN.D., YakubovskayaAYa, DenisenkoV.A., AnufrievVPh. (2006) Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anion. Synthesis of echinamine A – a metabolite produced by the sea urchin Scaphechinus mirabilis.Tetrahedron Letters, 47, 1385–1387.
7.
PelageevD.N., PanchenkoM.N., PokhiloN.D., DenisenkoV.A., AnufrievVPh. (2008) Synthesis of lomazarin and norlomazarin, pigments from Lomandra hastilis.Chemistry of Natural Compounds, 44, 719–723.
8.
PelageevD.N., PanchenkoM.N., PokhiloN.D., AnufrievVPh. (2010) Synthesis of 2,2'-(ethane-1,1-diyl)bis(3,5,6,7,8-pentahydroxy-1,4-naphthoquinone), a metabolite of the sea urchins Spatangus purpureus, Strongylocentrotus intermedius, and S. droebachiensis. Russian Chemical Bulletin, International Edition, 59, 1472–1476.
9.
PokhiloN.D., DraganS.V., AnufrievVPh. (2011) Revision of the structure of cuculoquinone to 3,3'-bis(6-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone) and confirmation of the proposed structure by synthesis. Tetrahedron Letters, 52, 3651–3653.
10.
ShestakO.P., AnufrievVPh, NovikovV.L. (2014) Preparative production of spinochrome E, a pigment of different sea urchin species. Natural Product Communications, 9, 953–956.
11.
BalanevaN.N., ShestakO.P., AnufrievVPh, NovikovV.L. (2016) Synthesis of spinochrome D, a metabolite of various sea-urchin species. Chemistry of Natural Compounds, 52, 213–217.
12.
ShestakO.P., BalanevaN.N., NovikovV.L. (2016) Preparative synthesis of spinochrome D, a pigment of different sea urchin species. Natural Product Communications, 11, 1307–1310.
13.
PokhiloN.D., AnufrievVPh. (2016) Simple synthesis of spinochrome C, a sea-urchin pigment. Chemistry of Natural Compounds, 52, 939–940.
14.
MelmanG.I., BorisovaK.L., PokhiloN.D., MakhankovV.V., AnufrievVPh. (2016) Unexpected conversion of echinochrome to brominated spinochrome D. Synthesis of 2-amino-3,6,7-trihydroxynaphthazarin produced by the sea urchins Strongylocentrotus nudus and Psammechinus miliaris.Tetrahedron Letters, 57, 736–738.
15.
PelageevD.N., AnufrievVPh. (2016) Synthesis of mirabiquinone A: a biquinone from the sea urchin Scaphechinus mirabilis and related compounds. Synthesis, 48, 761–764.
16.
ParisotD., DevysM., BarbierM. (1990) Naphthoquinone pigments related to fusaribin from the fungus Fusarium solani.Microbios, 64, 31–47.
17.
MezentsevA.G., AkimenkoV.K. (1998) Naphthoquinone metabolites of the fungi. Phytochemistry, 47, 935–959.
18.
YamamotoY., MatsubaraH., KinoshitaY., KinoshitaK., KoyamaK., TakahashiK., AhmadjiamV., KurokawaT., YoshimuraI. (1996) Naphthazarin derivatives from cultures of the lichen Cladonia cristatella.Phytochemistry, 43, 1239–1242.
19.
Ernst-RussellM.A., ElixJ.A., ChaiC.L.L., RiveM.J., WardlawJ.H. (2000) The structure and stereochemistry of coronatoquinone, a new pyranonaphthazarin from the lichen Pseudocyphellaria coronata.Australian Journal of Chemistry, 53, 303–306.
20.
MooreR.E., SinghI., ChangC.W.J., ScheuerP.J. (1967) Polyhydroxynaphthoquinones. Preparation and hydrolysis of methoxyl derivatives. Tetrahedron, 23, 3271–3305.
21.
GerberN.N., WieclawekB. (1966) The structures of two naphthoquinone pigments from an Actinomycete.Journal of Organic Chemistry, 31, 1496–1498.
22.
HuotR., BrassardP. (1974) Friedel-Crafts condensations with maleic anhydrides. The synthesis of polyhydroxylated naphthoquinones. Canadian Journal of Chemistry, 54, 838–842.
BruceD.B., ThomsonR.H. (1955) Quinones. Part V. The chemistry of naphthazarin. Journal of the Chemical Society, 1089–1096.
25.
DeWolfeR.H. (1970) Carboxylic Ortho Acid Derivatives: Preparation and Synthetic Applications, Academic Press, New York, London.
26.
MezheritskiiV.V., OlechnovitchE.P., DorofeenkoG.N. (1973) The properties of ortho ethers and their application in organic synthesis. Russian Chemical Review, 17, 896–940.
27.
AnufrievVPh, NovikovV.L., MalinovskayaG.V., GlazunovV.P. (1997) A convenient method for the selective alkylation of β-OH groups of 2(3)-hydroxyjuglones and hydroxynaphthazarins. Synthetic Communications, 27, 119–126.
28.
AnufrievVPh, TchizhovaAYa, DenisenkoV.A., NovikovV.L. (1993) The chemistry of naphthazarin derivatives. I. Reactions of 2-hydroxy-naphthazarins with the saturated aldehydes. Russian Journal of Organic Chemistry, 29, 2008–2017.
29.
DonaldsonN. (1960) TheChemistry and Technology of Naphthalene Compounds.Arnold, London.
30.
MalinovskayaG.V., TchizhovaAYa, AnufrievVPh. (1999) The chemistry of naphthazarin derivatives. 4. A simple preparative synthesis of mompain. Russian Chemical Bulletin, 48, 1010–1011.
31.
YakubovskayaAYa, PokhiloN.D., MishchenkoN.P., AnufrievVPh. (2007) Spinazarin and ethylspinazarin, pigments of the sea urchin Scaphechinus mirabilis.Russian Chemical Bulletin. International Edition, 56, 819–822.
32.
BerdyshevD.V., GlazunovV.P., YakubovskayaAYa, KocherginaTYu, AnufrievVPh. (2006) Calculation of frequencies of normal vibrations and interpretation of IR spectra for 2,3-dihydro-3-O-(1,4-naphthoquinon-2-yl)-2-oxo-1,4-naphthoquinone derivatives. Journal of the Applied Spectroscopy, 73, 798–806.
33.
ArnoneA., MerliniL., NasiniG., de PavaO.V. (2007) Direct amination of naphthazarin, juglone and some derivatives. Synthetic Communications, 37, 2569–2577.
34.
NatoriS., InouyeY., NishikawaH. (1967) The structures of mompain and deoxyhelicobasidin and the biosynthesis of helicobasidin, quinonoid metabolites of Helicobasidium mompa Tanaka.Chemical and Pharmaceutical Bulletin, 15, 380–390.
35.
ChangC.W.J., MooreR.E., ScheuerP.J. (1964) The structure of spinochrome M. Journal of the American Chemical Society, 86, 2959–2961.
