Lichen depsides

Seshadri et al. " used the reagent successfully for the synthesis of lichen depsides, for example (3, methyl evemate). Such esters previously had been prepared by... 

L-Leucyl-L-alanylglycine-L-valine, 517 L-Leucyl-L-methionine amide, 745 Levopimaric acid, 37 Levulinic add, 564-566 Lichen depsides, 232 Liebemiann-Butchard test, 1118 Limonene, 567, 646, 749-75Q, 922,1020 Linalool, 499 Linalool (R and S), 809 Lindlar catalyst, 566-567,1277 Unoleic add, 818, 1008, 1052, 1155, 1264, 1265, 1286 isomers, 260... 

Table 11. Mass spectrometric fragments of lichen depsides ...

Table 11 contains the MS fragments of lichen depsides and Table 12 the molecular weights and formulae of lichen substances. 

Elix JA, Ferguson BA (1977) Synthesis of the lichen depside 2-0-methylconfluentic acid. Aust J Chem 30 373-385... 

Elix JA, Ferguson BA (1978) Synthesis of the lichen depsides, olivetoric acid, confluentic acid and 4-0-methylolivetoric acid. Aust J Chem 31 1041-1045 Elix JA, Gaul KL (1986) The interconversion of the lichen depsides para- and metascrobiculin, and the biosynthetic implications. Aust J Chem 39 613-624 Elix JA, Jayanthi VK (1977) 5-0-Methylhiascic acid, a new tridepside from Australian lichens. Aust J Chem 30 2695-2704... 

Elix JA, Jayanthi VK (1986) Synthesis of the lichen depsides miriquidic acid and normiriquidic acid. Aust J Chem 39 791-797... 

Elix JA, Jayanthi VK (1987a) Synthetic confirmation of the structure of the lichen benzyl esters alectorialic and barbatolic acids. Aust J Chem 40 1841-1850 Elix JA, Jayanthi VK (1987b) The isolation and synthesis of the lichen depside 4-0-demethylmicrophyllinic acid. Aust J Chem 40 1851-1859... 

Elix JA, Lajide L (1984b) Synthesis of the lichen depsides pseudocyphellarin A and B. Aust J Chem 37 2153-2157... 

Elix JA, Wardlaw JH (1987) Synthesis of lichen para-sphaerophorol depsides. Aust J Chem 40 425-429 Elix JA, Whitton AA (1989) Synthesis of the lichen depsides glomelliferic acid, loxodellic acid, glomellic acid, their 4-0-demethyl analogues and oxostenosporic acid. Aust J Chem 42 1969-1981... 

Huneck S (1984b) Tert-butanolysis of lichen depsides. Phytochemistry 23 2697-2698... 

Kurokawa S, Elix JA, Watson PL, Sargent MV (1971) Parmelia notatay a new lichen species producing two new depsidones. J Jpn Bot 46 33-38 Kutney JP, Sanchez IH, Yee TH (1974) Mass spectral fragmentation studies in usnic acid and related compounds. Org Mass Spectrom 8 129-146 Laake Oy (1960) Institutional advertising of the La e Oy Pharmaceutical Manufacturers, Turku, Finland Lajide L (1984) Lichen depsides, depsidones and diphenyl ethers isolation, structure determination and synthesis. Thesis, Australian National Univ, Canberra Lam JKK, Sargent MV, Elix JA, Smith DO N (1972) Synthesis of valsarin and 5,7-dichloroemodin. J Chem Soc Perkin Trans 1 1466-1470... 

Sundholm EG, Huneck S (1980) C NMR-spectra of lichen depsides, depsidones and depsones. 1. Compounds of the orcinol series. Chem Scripta 16 197-200... 

Whitton AA (1989) Approaches to the synthesis of ketonic lichen depsides. Thesis, Australian National Univ, Canberra... 

The more classical chemical procedures of degradation and total synthesis also developed apace with the use of newer reagents and synthetic methods. For instance, the use of condensing reagents trifluoroacetic anhydride and dicyclohexyl-carbodiimide makes the preparation of lichen depsides a relatively straightforward procedure, so that total synthesis is now a common means of strucmral confirmation. 

Cardarelli M, Serino G, Campanella L et al (1997) Antimitotic effects of usnic acid on different biological systems. Cell Mol Life Sci 53 667-672 Cheng B, Cao S, Vasquez V et al (2013) Identification of anziaic acid, a lichen depside from Hypotrachyna sp., as a new topoisomerase poison inhibitor. PLoS One 8(4) e60770 Cohen PA, Towers GHN (1995) Anthraquinones and phenanthroperylenequinones from Nephroma laevigatum. J Nat Prod 58 520-526... 

Culberson, C. F., and M. J. Dibben 2-O-Methylperlatolic and 2 -0-methylperlatolic Acids Two New Lichen Depsides from Pertusaria. Bryologist 75, 362 (1972). Culberson, C. F., and T. L. Esslinger 4-0-Methylolivetoric and Loxodellic Acids. New Depsides from New Species of Brown Parmeliae. Bryologist 79, 42 (1976). Culberson, C. F., and M. E. Hale, Jr. 4-0-Demethylnotatic Acid, a New Depsidone in Some Lichens Producing Hypoprotocetraric Acid. Bryologist 76, 77 (1973). Culberson, C. F., and H. Hertel 2 -0-Methylanziaic Acid, a New Depside in Lecidea diducens and Lecidea speirodes. Bryologist 75, 372 (1972). 

Synthesis of the Lichen Depsides, Olivetoric Acid, Confluence Acid and 4-0-... 

SuNDHOLM, E. G., and S. Huneck C NMR-Spectra of Lichen Depsides, Depsidones and Depsones. 1. Compounds of the Orcinol Series. Chemica Scripta 16, 197 (1980). 

Fig. 1. Basic structural formulae of the main classes of lichen depsides.

Yamazaki, M., and Shibata, S. (1966). Biosynthesis of lichen substances. II. Participation of Cj-unit to the formation of -orcinol type lichen depside. Chem. Pharm. Bull. 14,96. 

Fuzikawa found (1939) that the phenols and their derivatives, components of lichen depsides and depsidones, possess remarkably strong antiseptic qualities. 

Huneck et al. 408) have investigated the thermal decomposition of lichen depsides. The main decomposition products were decarboxylated... 

Elix JA, Barclay CE, David F, Criffin FK, Hill AM, McConnell DB, Wardlaw JH (1993) Synthesis of Further Lichen Depsides. Aust J Chem 46 301... 

Elix JA, Gaul KL (1986) The Interconversion of the Lichen Depsides para- and meta-Scrobiculin, and the Biosynthetic Implications. Aust J Chem 39 613... 

Elix JA, Jayanthi VK (1987) The Isolation of the Lichen Depside 4-O-Demethyl-microphyllinic Acid. Aust J Chem 40 1851... 

Huneck S (1984) TerZ-butanolysis of Lichen Depsides. Phytochemistry 23 2697... 

Huneck S, Schmidt J, Tabacchi R (1989) Thermal Decomposition of Lichen Depsides Z Naturforsch 44b 1283... 

Huovinen K, Hiirmala P, Ottoila P, Hiltunen R, Von Schantz M (1987) Fast Atom Bombardment Mass Spectrometry in the Characterization of Lichen Depsides. Poster at the Univ Leiden... 

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