Determination of the absolute configuration of 6-alkylated α-pyrones from Ravensara crassifolia by LC-NMR

Phytochemical Analysis

Volumn 14, Issue 1, 2003, Pages 34-39

  Queiroz, E F ^a   Wolfender, J L ^a   Raoelison, G ^a   Hostettmann, K ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Absolute configuration; LC MS; LC NMR; Mosher's esters; Ravensara crassifolia; pyrones

Indexed keywords

DEUTERIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS;

ABSOLUTE CONFIGURATION; CRUDE REACTION MIXTURES; ESTER DERIVATIVES; LC-MS; LC-NMR; MOSHER ESTER; MOSHER'S METHOD; RAPID METHOD; RAVENSARA CRASSIFOLIUM; Α-PYRONE;

ESTERS;

2 PYRONE DERIVATIVE; ACETONITRILE; DEUTERIUM OXIDE; ESTER DERIVATIVE; SOLVENT;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; FLUID SHIFT; MASS SPECTROMETRY; NONHUMAN; PLANT; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; RATING SCALE; RAVENSARA; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SENSITIVITY ANALYSIS;

RAVENSARA; RAVENSARA CRASSIFOLIA;

EID: 0037273103     PISSN: 09580344     EISSN: None     Source Type: Journal    
DOI: 10.1002/pca.684     Document Type: Article

References (15)

1. Dale JA and Mosher HS. 1968. Nuclear magnetic resonance non-equivalence of diastereoisomeric esters of α-substituted phenylacetic acids for the determination of stereochemical purity. J Am Chem Soc 90: 3732-3738.
2. Dale JA and Mosher HS. 1973. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate. J Am Chem Soc 95: 512-519.
3. Dale JA, Dull DL and Mosher HS. 1969. α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 34: 2543-2549.
4. Fiud JC, Horeau A and Kagan HB. 1977. Methods for the determination of absolute configuration. In Stereochemistry, Vol. 3, Kagan HB (ed.). George Thieme: Stuttgart: 9-21.
5. Gu ZM, Zeng L, Fang XP, Colman-Saizarbitoria T, Huo M and McLaughlin JL. 1994. Determining absolute configurations of stereo-centres in Annonaceous acetogenins through formaldehyde acetal derivatives and Mosher's ester methodology. J Org Chem 59: 5162-5172.
6. Harada N and Nakanishi K. 1983. Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry. University Science Books: Mill Valley.
7. Jeong SJ, Miyamoto T, Inagaki M, Kine YC and Higuchi R. 2000. Three novel sesquiterpene alkaloids from Cyperus rotundus. J Nat Prod 60: 673-675.
8. Ohtani I, Kusumi T, Kashman Y and Kakisawa H. 1991. High-field FT NMR application of Mosher method. The absolute configurations of marine terpenoids. J Am Chem Soc 113: 4092-4096.
9. Rasmussen HB, Christensen SB, Kvist LP, Kharazmi A and Huansi AG. 2000. Absolute configuration and anti-protozoal activity of minquartynoic acid. J Nat Prod 63: 1295-1296.
10. Raoelison GE, Terreaux C, Queiroz EF, Zsila F, Simonyi M, Antus S, Randriantosona A and Hostettmann K. 2001. Absolute configuration of two new 6-alkylated-α-pyrones from Ravensara crassifolia. Helv Chim Acta 84: 3470-3476.
11. Raoelison GE, Terreaux C, Queiroz EF, Zsila F, Simonyi M, Antus S, Randriantosona A and Hostettmann K. 2003. Erratum: Absolute configuration of two new 6-alkylated-α-pyrones from Ravensara crassifolia. Helv Chim Acta (in press).
12. Smallcombe SH, Patt SL and Keiffer PA. 1995. WET solvent suppression and its application to LC-NMR and high-resolution NMR spectroscopy. J Mag Reson A 117: 295-303.
13. Sullivan GR, Dale JA, Dull DL and Mosher HS. 1973. Correlation of configuration and 19F chemical shifts of α-methoxy-α-trifluoromethylphenylacetate derivatives. J Org Chem 38: 2143-2147.
14. Trost BM, Belletire JL, Godleski S, McDougal MC and Balkovec JM. 1986. On the use of the O-methylmandelate ester for establishment of absolute configuration of secondary alcohols. J Org Chem 51: 2370-2374.
15. Wolfender JL, Ndjoko K and Hostettmann K. 2001. The potential of LC-NMR in phytochemical analysis. Phytochem Anal 11: 1-22.