Lactones 39. 1 Chemical and microbial synthesis of lactones from (-)-α- and (+)-β-thujone

Phytochemistry Letters

Volumn 5, Issue 2, 2012, Pages 340-345

  Gniłka, Radosław ^a   Szumny, Antoni ^a   Białońska, Agata ^b   Wawrzeńczyk, Czesław ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF WROC AW   (Poland)

Author keywords

and thujone; Baeyer Villiger oxidation; Terpenoid lactones; Thuja occidentalis

Indexed keywords

ABSINTHOL; BETA THUYONE; BICYCLO COMPOUND; CEDAR LEAF OIL; CYCLOPROPANE; LACTONE DERIVATIVE;

ARTICLE; BAEYER VILLIGER REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; FUSARIUM; FUSARIUM AVENACEUM; FUSARIUM OXYSPORUM; HETERONUCLEAR SINGLE QUANTUM COHERENCE; INFRARED SPECTROSCOPY; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

THUJA OCCIDENTALIS;

EID: 84860530410     PISSN: 18743900     EISSN: 18767486     Source Type: Journal    
DOI: 10.1016/j.phytol.2012.02.015     Document Type: Article

References (30)

1. Y. Asakawa Recent advances in phytochemistry of bryophytes-acetogenins, terpenoids and bis(bibenzyl)s from selected Japanese, Taiwanese, New Zealand, Argentinean and European liverworts Phytochemistry 56 2001 297 312
2. C.N. Banwell, and N. Sheppard (H,H) coupling constants in the nuclear magnetic resonance spectra of hydrocarbon groupings Discuss. Faraday Soc. 34 1962 115 126
3. M. Barfield, and B. Chakrabarti Long-range proton spin-spin coupling Chem. Rev. 69 1969 757 778
4. CrysAlis 'RED', 2009. Oxford Diffraction Ltd.; Abingdon, Oxfordshire, England.
5. I. Dams, A. Białońska, Z. Ciunik, and C. Wawrzeńczyk Synthesis of terpenoid lactones with the p-menthane system Eur. J. Org. Chem. 12 2004 2662 2668
6. Dams, I.; Białońska, A.; Ciunik, Z.; Wawrzeńczyk, C.; 2012. Lactones 38. Synthesis and odoriferous properties of p-menthane lactones. Flavour Frag. J.; doi:10.1002/ffj.3085, in press.
7. M. De Leo, M. Beatriz Vera Saltos, B. Fabiola Nranjo Puente, N. De Tommasi, and A. Braca Sesquiterpenes and diterpenes from Ambrosia arborescens Phytochemistry 71 2010 804 809
8. B.M. Fraga Natural sesquiterpenoids Nat. Prod. Rep. 19 2002 650 672
9. V. Hach, R.W. Lockhart, E.C. MacDonald, and D.M. Cartlidge On the isolation of (+)3-thujone Can. J. Chem. 41 1971 1762 1764
10. K. Hüsnü Can Baser, and G. Buchbauer Handbook of Essential Oils: Science, Technology and Applications 2010 CRC Press New York
11. 13C NMR Nat. Prod. Commun. 4 2009 1113 1118
12. O. Koul Insect feeding deterrents in plants Indian Rev. Life Sci. 2 1982 97 125
13. S.M. Kupchan, M.A. Eakin, and A.M. Thomas Tumor inhibitors 69. Structure-cytotoxicity relations among the sesquiterpene lactones J. Med. Chem. 14 1971 1147 1152
14. M.D. Mihovilovic, B. Müller, and P. Stanetty Monooxygenase-mediated Baeyer-Villiger oxidations Eur. J. Org. Chem. 22 2002 3711 3730
15. K. Mislow, and J. Brenner Stereospecificity of the Baeyer-Villiger rearrangement J. Am. Chem. Soc. 75 1952 2318 2322
16. J. Nawrot, I. Dams, and C. Wawrzeńczyk Feeding deterrent activity of terpenoid lactones with a p-menthane system against stored-product pests Stored Prod. Res. 45 2009 221 225
17. M.F. Neerman Sesquiterpene lactones: a diverse class of compounds found in essential oils possessing antibacterial and antifungal properties Int. J. Aromather. 13 2003 114 120
18. D.M. Norris Anti-feeding compounds W.S. Bowers, W. Ebing, I.R. Fukuto, D. Martins, R. Weigler, I. Yamamoto, Chemistry of Plants Protection, Sterol, Biosynthesis, Inhibitors and Antifeeding Compounds 1982 Springer Verlag Berlin 99 146
19. W. Oppolzer, A. Pimm, B. Stammen, and W.E. Hume Palladium-catalysed intramolecular cyclisations of olefinic propargylic carbonates and application to the diastereoselective synthesis of enantiomerically pure (-)-α-thujone Helv. Chim. Acta 80 1997 623 639
20. E. Paruch, Z. Ciunik, and C. Wawrzeńczyk Lactones. 9. Synthesis of terpenoid lactones active insect antifeedants J. Agric. Food Chem. 48 2000 4973 4977
21. B. Ratuś, W. Gładkowski, and C. Wawrzeńczyk Lactones 32 [1] new aspects of the application of Fusarium strains to production of alkylsubstituted ε-lactones Enzyme Microb. Technol. 45 2009 156 163
22. J. Rohloff, R. Mordal, and S. Dragland Chemotypical variation of tansy (Tanacetum vulgare L.) from 40 different locations in Norway J. Agric. Food Chem. 52 2004 1718 1742
23. L.M. Schoonhoven Biological aspects of antifeedants Entomol. Exp. Appl. 31 1982 57 69
24. J.M. Schwab Stereochemistry of an enzymatic Baeyer-Villiger reaction. Application of deuterium NMR J. Am. Chem. Soc. 103 1981 1876 1878
25. J.M. Schwab, W.-b. Li, and L.P. Thomas Cyclohexanone oxygenase: stereochemistry, enantioselectivity, and regioselectivity of an enzyme-catalyzed Baeyer-Villiger reaction J. Am. Chem. Soc. 105 1983 4800 4808
26. G.M. Sheldrick A short history of SHELX Acta Crystallogr. A 64 2008 112 122
27. N.S. Sirisoma, K.M. Höld, and J.E. Casida α- and β-thujones (herbal medicines and food additives): synthesis and analysis of hydroxy and dehydro metabolites J. Agric. Food Chem. 49 2001 1915 1921
28. M. Szczepanik, I. Dams, and C. Wawrzeńczyk Terpenoid lactones with the p-menthane system as feeding deterrents to the lesser mealworm Alphitobius diaperinus Entomol. Exp. Appl. 128 2008 337 345
29. A. Szumny, and C. Wawrzeńczyk Lactones, part 28: [1] a new approach for the synthesis of α-methylene lactones from alkenes Synlett 10 2006 1523 1526
30. D. Tsiri, K. Graikou, L. Pobłocka-Olech, M. Krauze-Baranowska, C. Spyropoulos, and I. Chinou Chemosystematic value of the essential oil composition of Thuja species cultivated in Poland - antimicrobial activity Molecule 14 2009 4707 4715