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Volumn 65, Issue 11, 2000, Pages 3551-3554

A short and efficient enantiospecific synthesis of (+)-(2R,6S)-cis-γ- irone via a highly diastereoselective protonation

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[No Author keywords available]

Indexed keywords

ESSENTIAL OIL;

EID: 0034595960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991903h     Document Type: Note
Times cited : (23)

References (37)
  • 1
    • 0003455364 scopus 로고
    • Springer-Verlag Berlin Heidelberg
    • (a) Ohloff, G. In Scent and Fragrances; Springer-Verlag Berlin Heidelberg, 1994; p 164.
    • (1994) Scent and Fragrances , pp. 164
    • Ohloff, G.1
  • 9
    • 84954950447 scopus 로고
    • Syntheses leading to a cis:trans mixture of (±)γ-irones: (a) Kitahara, T.; Tanioa, K.; Mori, K. Agric. Biol. Chem. 1983, 47, 581. (b) Leyendecker, F.; Comte, M.-T. Tetrahedron 1987, 43, 85. (c) Kawanobe, T.; Iwamoto, M.; Kogami, K.; Matsui, M. Agric. Biol. Chem. 1987, 51, 791.
    • (1983) Agric. Biol. Chem. , vol.47 , pp. 581
    • Kitahara, T.1    Tanioa, K.2    Mori, K.3
  • 10
    • 0001849067 scopus 로고
    • Syntheses leading to a cis:trans mixture of (±)γ-irones: (a) Kitahara, T.; Tanioa, K.; Mori, K. Agric. Biol. Chem. 1983, 47, 581. (b) Leyendecker, F.; Comte, M.-T. Tetrahedron 1987, 43, 85. (c) Kawanobe, T.; Iwamoto, M.; Kogami, K.; Matsui, M. Agric. Biol. Chem. 1987, 51, 791.
    • (1987) Tetrahedron , vol.43 , pp. 85
    • Leyendecker, F.1    Comte, M.-T.2
  • 11
    • 0001173631 scopus 로고
    • Syntheses leading to a cis:trans mixture of (±)γ-irones: (a) Kitahara, T.; Tanioa, K.; Mori, K. Agric. Biol. Chem. 1983, 47, 581. (b) Leyendecker, F.; Comte, M.-T. Tetrahedron 1987, 43, 85. (c) Kawanobe, T.; Iwamoto, M.; Kogami, K.; Matsui, M. Agric. Biol. Chem. 1987, 51, 791.
    • (1987) Agric. Biol. Chem. , vol.51 , pp. 791
    • Kawanobe, T.1    Iwamoto, M.2    Kogami, K.3    Matsui, M.4
  • 12
    • 0023929718 scopus 로고
    • Stereoselective syntheses of (±)-cis-γ-irone: (a) Nussbaumer, C.; Fràter, G. Helv. Chim. Acta 1988, 71, 619. (b) Monti, H.; Lavai, G.; Féraud, M. Eur. J. Org. Chem. 1999, 1825.
    • (1988) Helv. Chim. Acta , vol.71 , pp. 619
    • Nussbaumer, C.1    Fràter, G.2
  • 13
    • 0032801786 scopus 로고    scopus 로고
    • Stereoselective syntheses of (±)-cis-γ-irone: (a) Nussbaumer, C.; Fràter, G. Helv. Chim. Acta 1988, 71, 619. (b) Monti, H.; Lavai, G.; Féraud, M. Eur. J. Org. Chem. 1999, 1825.
    • (1999) Eur. J. Org. Chem. , pp. 1825
    • Monti, H.1    Lavai, G.2    Féraud, M.3
  • 15
    • 0342736978 scopus 로고    scopus 로고
    • unpublished results
    • (b) Monti, H. unpublished results.
    • Monti, H.1
  • 19
    • 0023273842 scopus 로고
    • 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (Solladié, G.; Hutt, J. J. Org. Chem. 1987, 52, 3560). (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-2 (Iio, H.; Monden, M.; Okada, K.; Tokoroyama, T. J. Chem. Soc., Chem. Commun. 1987, 358. See also: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682). (equation presented)
    • (1987) J. Org. Chem. , vol.52 , pp. 3560
    • Solladié, G.1    Hutt, J.2
  • 20
    • 37049072971 scopus 로고
    • 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (Solladié, G.; Hutt, J. J. Org. Chem. 1987, 52, 3560). (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-2 (Iio, H.; Monden, M.; Okada, K.; Tokoroyama, T. J. Chem. Soc., Chem. Commun. 1987, 358. See also: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682). (equation presented)
    • (1987) J. Chem. Soc., Chem. Commun. , pp. 358
    • Iio, H.1    Monden, M.2    Okada, K.3    Tokoroyama, T.4
  • 21
    • 33847089555 scopus 로고
    • equation presented
    • 4 led to (+)-(R)-6-methylcyclohex-2-en-1-one (Solladié, G.; Hutt, J. J. Org. Chem. 1987, 52, 3560). (b) Treatment of this ketone with methyllithium, followed by oxidation with pyridinium chlorochromate (PCC), afforded (+)-2 (Iio, H.; Monden, M.; Okada, K.; Tokoroyama, T. J. Chem. Soc., Chem. Commun. 1987, 358. See also: Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682). (equation presented)
    • (1977) J. Org. Chem. , vol.42 , pp. 682
    • Dauben, W.G.1    Michno, D.M.2


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