Synthesis and odor of chiral partial structures of β-vetivone, part 2

Chirality

Volumn 11, Issue 2, 1999, Pages 133-138

  Spreitzer, Helmut ^a   Piringer, Iris ^a   Pichler, Andrea ^a   Holzer, Wolfgang ^a   Ruzicka, Jana ^a   Widhalm, Michael ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

vetivone; 13C NMR spectroscopy; 1HNMR spectroscopy; Circular dichroism; Structure odor relationship; Vetiver oil

Indexed keywords

BETA VETIVONE; CYCLOPENTANE; ESSENTIAL OIL; PERFUME; UNCLASSIFIED DRUG; VETIVER OIL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ODOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 0032948440     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:2<133::AID-CHIR9>3.0.CO;2-E     Document Type: Article

References (21)

1. Ohloff G. Scent and fragrances. The fascination of odors and their chemical perspectives. Berlin-Heidelberg-New York: Springer; 1990. p 172-173.
2. Mookherjee BD, Trenkle RW, Wilson RA. New insights in the three most important natural fragrance products: wood, amber and musk. In: Woidich H, Buchbauer G, editors. Proceedings of the 12th International Congress of Essential Oils Fragrances and Flavours. Austria Ass. of Flavour and Fragrance Inc., Vienna, Austria; 1992, p. 234-262.
3. 4-mediated intramolecular C-H-insertion: steric and electronic effects. J Am Chem Soc 1986;108:7686-7693.
4. Spreitzer H, Piringer I, Pichler A. Holzer W, Schreder P, Widhalm M. Synthesis and odor of chiral partial structures of β-vetivone, part I. Chirality 1999;11:14-20.
5. Murai A, Taketsuru H, Masamune T. The Synthesis of (±)-Glutinosone. Bull Chem Soc Jpn 1980;53:1049-1056.
6. Willis BJ, Eilerman RG. Fragrance Composition Comprising Substituted Cyclohexane Derivatives. U.S. Patent 4,326,996. 1982.
7. Schulte-Elte KH, Strickler H, Gautschi F, Pickenhagen W, Gadola M, Limacher J, Müller BL, Wuffli F, Ohloff G. Synthesen und Cyclisierungsreaktionen der Pseudo-damascone-Ein neuer Zugang zu α-Damasconverbindungen. Liebigs Ann Chem 1975;484-508.
8. Seebach D. Structure and reactivity of lithium enolates from pinacolone for the selective C-alkylation of peptides. Difficulties and possibilities through complex structures. Angew Chem 1988;100:1685-1715.
9. Stork G, Danheiser RL, Ganem B. Spiroannelation of enol ethers of cyclic 1,3-diketones. A simple stereospecific synthesis of β-vetivone. J Am Chem Soc 1973;95:3414-3415.
10. Neuhaus D, Williamson MP. The nuclear overhauser effect in structural and conformational analysis. New York: VCH Publishers: 1989. p 211-252.
11. Bax A, Subramanian S. Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy. J Magn Reson 1986;67: 565-569.
12. Sarkar SA, Bax A. A simple and sensitive one-dimensional NMR technique for correlation of proton and carbon chemical shifts. J Magn Reson 1985;62:109-112.
13. Patt S, Shoolery JN. Attached proton test for carbon-13 NMR. J Magn Reson 1982;46:535-539.
14. 13C couplings. J Magn Reson 1984;57:314-318.
15. Jippo T, Kamo O, Nagayama K. Determination of long-range proton-carbon 13 coupling constants with selective two-dimensional INEPT. J Magn Reson 1986;66:344-348.
16. SYBYL [computer program]. Version 6.3. St. Louis: Tripos Inc.; 1996.
17. Johnson CR, Schoeck CW, Shanklin JR. The mechanisms of nucleophilic alkylidene transfer by sulfonium and oxosulfonium ylides. J Am Chem Soc 1973;95:7424-7431.
18. Preite MD, Zinczuk J, Colombo MI, Bacigaluppo JA, Gonzáles-Sierra M, Rúveda EA. Resolution and absolute configuration of a tricyclic lactone. Tetrahedron Asymmetry 1993;4:17-20.
19. Paquette LA, Deaton DN, Endo Y, Poupart MA. Studies directed toward the total synthesis of cerorubenic acid-III. J Org Chem 1993;58: 4262-4273.
20. Gawronski JK. Circular dichroism and stereochemistry of chiral conjugated cyclohexenones. Tetrahedron 1982;38:3-26.
21. Kirk DN. The chiroptical properties of carbonyl compounds. Tetrahedron 1986;42:777-818.