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Volumn 52, Issue 11, 1996, Pages 3879-3888

A new practical synthesis of (+)-grandisol from (+)-citronellol using an intramolecular carbenoid cyclization

Author keywords

[No Author keywords available]

Indexed keywords

GRANDISOL; PHEROMONE; UNCLASSIFIED DRUG;

EID: 0029989533     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00175-5     Document Type: Article
Times cited : (22)

References (30)
  • 7
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    • d) Narasaka, K., Kusama, H., and Hayashi, Y. Bull. Chem. Soc. Jpn., 1991, 64, 1471; for references to earlier enantioselective grandisol syntheses, see Hoffmann, N. and Scharf, H. -D. Liebigs Ann. Chem., 1991, 1273.
    • (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 1471
    • Narasaka, K.1    Kusama, H.2    Hayashi, Y.3
  • 8
    • 0041620878 scopus 로고
    • d) Narasaka, K., Kusama, H., and Hayashi, Y. Bull. Chem. Soc. Jpn., 1991, 64, 1471; for references to earlier enantioselective grandisol syntheses, see Hoffmann, N. and Scharf, H. -D. Liebigs Ann. Chem., 1991, 1273.
    • (1991) Liebigs Ann. Chem. , pp. 1273
    • Hoffmann, N.1    Scharf, H.-D.2
  • 9
    • 33947332848 scopus 로고
    • Enantiomerically pure (+)-citronellol is readily secured from (+)-pulegone, see Overberger, C. G. and Kaye, H. J J. Am. Chem. Soc., 1968, 89, 5640; or by enzymatic resolution, see Cambou, B. and Klibanov, A. M. J. Am. Chem. Soc., 1984, 106, 2687; for other methods and use in natural products synthesis, see Ho, T. -L. Enantioselective Synthesis. Natural Products from Chiral Terpenes, 1992, John Wiley & Sons, New York.
    • (1968) J. Am. Chem. Soc. , vol.89 , pp. 5640
    • Overberger, C.G.1    Kaye, H.J.2
  • 10
    • 0021753566 scopus 로고
    • Enantiomerically pure (+)-citronellol is readily secured from (+)-pulegone, see Overberger, C. G. and Kaye, H. J J. Am. Chem. Soc., 1968, 89, 5640; or by enzymatic resolution, see Cambou, B. and Klibanov, A. M. J. Am. Chem. Soc., 1984, 106, 2687; for other methods and use in natural products synthesis, see Ho, T. -L. Enantioselective Synthesis. Natural Products from Chiral Terpenes, 1992, John Wiley & Sons, New York.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 2687
    • Cambou, B.1    Klibanov, A.M.2
  • 11
    • 0003824820 scopus 로고
    • John Wiley & Sons, New York
    • Enantiomerically pure (+)-citronellol is readily secured from (+)-pulegone, see Overberger, C. G. and Kaye, H. J J. Am. Chem. Soc., 1968, 89, 5640; or by enzymatic resolution, see Cambou, B. and Klibanov, A. M. J. Am. Chem. Soc., 1984, 106, 2687; for other methods and use in natural products synthesis, see Ho, T. -L. Enantioselective Synthesis. Natural Products from Chiral Terpenes, 1992, John Wiley & Sons, New York.
    • (1992) Enantioselective Synthesis. Natural Products from Chiral Terpenes
    • Ho, T.-L.1
  • 13
    • 0000932229 scopus 로고
    • For an elegant example of construction of a quaternary center with retention of configuration by means of an intramolecular carbenoid cyclization see Taber, D. F., Petty, E. H., and Raman, K. J. Am. Chem. Soc., 1985, 107, 196.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 196
    • Taber, D.F.1    Petty, E.H.2    Raman, K.3
  • 18
    • 85022461617 scopus 로고    scopus 로고
    • Section C
    • A full crystallographic report on 6 and 13 has been submitted to Acta Crystallographica, Section C.
    • Acta Crystallographica
  • 22
    • 0343201050 scopus 로고
    • b) Rosini, G., Carloni, P., Iapalucci, M. C., and Marotta, E. Tetrahedron: Asymmetry, 1990, 1, 751. The melting point of the enantiomerically pure alcohol 10 has erroneously been reported as 56-57°C in these publications; the correct melting point is 75-77°C (personal communication from Prof. Rosini, to whom the authors are indebted for a generous sample of the product ).
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 751
    • Rosini, G.1    Carloni, P.2    Iapalucci, M.C.3    Marotta, E.4
  • 23
    • 85030195255 scopus 로고    scopus 로고
    • note
    • -1 more stable than 11. We thank Prof. Elaine R. Maia for performing the calculations.
  • 25
    • 0038221302 scopus 로고
    • Pure enantiomer : a) Mori, K. Tetrahedron, 1978, 34, 915;
    • (1978) Tetrahedron , vol.34 , pp. 915
    • Mori, K.1
  • 26
    • 0000861107 scopus 로고
    • b) Webster, F. X. and Silverstein, R. M. J. Org Chem., 1986, 51, 5226; for the racemic form, see: c) Rosini, G., Marotta, E., Petrini, M., and Ballini, R. Tetrahedron, 1985, 41, 4633;
    • (1986) J. Org Chem. , vol.51 , pp. 5226
    • Webster, F.X.1    Silverstein, R.M.2
  • 27
    • 0001326264 scopus 로고
    • b) Webster, F. X. and Silverstein, R. M. J. Org Chem., 1986, 51, 5226; for the racemic form, see: c) Rosini, G., Marotta, E., Petrini, M., and Ballini, R. Tetrahedron, 1985, 41, 4633;
    • (1985) Tetrahedron , vol.41 , pp. 4633
    • Rosini, G.1    Marotta, E.2    Petrini, M.3    Ballini, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.