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Volumn 9, Issue 2, 1998, Pages 293-303

Novel stereocontrolled synthesis of the tricyclic lactone (1R,3R, 6R,9S)-6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.03,9]nonane

Author keywords

[No Author keywords available]

Indexed keywords

6,9 DIMETHYL 8 OXO 7 OXATRICYCLO[4.3.0.0 3,9]NONANE; LACTONE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

EID: 0032579175     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00641-1     Document Type: Article
Times cited : (12)

References (26)
  • 7
    • 0000254668 scopus 로고
    • Access to the trans-carveols 6 and 9 was accomplished by application of a two-step synthetic sequence (epoxidation-Wharton rearrangement) to the commercially available R-(-)-carvone and S-(+)-carvone respectively. For further details, see
    • Access to the trans-carveols 6 and 9 was accomplished by application of a two-step synthetic sequence (epoxidation-Wharton rearrangement) to the commercially available R-(-)-carvone and S-(+)-carvone respectively. For further details, see: Klein, E.; Ohloff, G. Tetrahedron 1963, 19, 1091-1099.
    • (1963) Tetrahedron , vol.19 , pp. 1091-1099
    • Klein, E.1    Ohloff, G.2
  • 8
    • 0007390202 scopus 로고
    • Enantiomerically pure (+)-trans-carveol 6 and (-)-trans-carveol 9 have been obtained from their 3,5-dinitrobenzoates following the Johnston procedure
    • Enantiomerically pure (+)-trans-carveol 6 and (-)-trans-carveol 9 have been obtained from their 3,5-dinitrobenzoates following the Johnston procedure: Johnston, R. G.; Read, J. J. J. Chem. Soc. 1934, 233-237.
    • (1934) J. Chem. Soc. , pp. 233-237
    • Johnston, R.G.1    Read, J.J.2
  • 9
    • 33751499786 scopus 로고
    • The Johnson ortho ester Claisen rearrangement of (-)-cis carveol has been studied previously: (a)
    • The Johnson ortho ester Claisen rearrangement of (-)-cis carveol has been studied previously: (a) Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650-657.
    • (1991) J. Org. Chem. , vol.56 , pp. 650-657
    • Ireland, R.E.1    Wipf, P.2    Armstrong, J.D.3
  • 11
    • 0345543843 scopus 로고    scopus 로고
    • note
    • The enantiomerically pure amide 10c has been obtained from (-)-trans-carveol 9 by application of a three-step sequence with 70% overall yield.
  • 12
    • 0344681681 scopus 로고    scopus 로고
    • note
    • 1H-NMR analysis of the crude reaction product corresponding to the transformation of carboxylic acid 10a into the amide 10c.
  • 13
    • 0345543844 scopus 로고    scopus 로고
    • note
    • Correspondence regarding the X-ray crystallographic determination should be addressed to Prof. Dr. Santiago Garcia-Granda, Universidad de Oviedo, Spain.
  • 14
    • 0023883986 scopus 로고
    • The oxidative cyclization of similar γ,δ-unsaturated acids belonging to the cis series have been studied previously: (a)
    • The oxidative cyclization of similar γ,δ-unsaturated acids belonging to the cis series have been studied previously: (a) Ireland, R. E.; Maienfisch, P. J. Org. Chem. 1988, 53, 640-651.
    • (1988) J. Org. Chem. , vol.53 , pp. 640-651
    • Ireland, R.E.1    Maienfisch, P.2
  • 16
    • 11944270778 scopus 로고
    • The oxidative degradation of the isopropenyl chain has numerous precedents in the literature; for a review, see
    • The oxidative degradation of the isopropenyl chain has numerous precedents in the literature; for a review, see: Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952.
    • (1995) Chem. Rev. , vol.95 , pp. 1877-1952
    • Zhu, G.-D.1    Okamura, W.H.2
  • 17
    • 0345112619 scopus 로고    scopus 로고
    • note
    • Satisfactory yields in the alkylation process were only obtained by a sudden increase of the reaction temperature (from -78°C to room temperature) after addition of the methyl iodide.
  • 21
    • 0345543841 scopus 로고
    • 'SHELX86'
    • Ed. Sheldrick, G. M.; Kruger, C.; Goddard, R., Clarendon Press, Oxford
    • Sheldrick, G. M. 'SHELX86'. In Crystallographic Computing 6. Ed. Sheldrick, G. M.; Kruger, C.; Goddard, R., Clarendon Press, Oxford, 1985.
    • (1985) In Crystallographic Computing 6
    • Sheldrick, G.M.1
  • 22
    • 0345112616 scopus 로고
    • 'SHELXL93'
    • Ed. Flack, H. D.; Parkanyi, P.; Simon, K. IUCr/Oxford University Press
    • Sheldrick, G. M. 'SHELXL93'. In Crystallographic Computing 6. Ed. Flack, H. D.; Parkanyi, P.; Simon, K. IUCr/Oxford University Press, 1993.
    • (1993) In Crystallographic Computing 6
    • Sheldrick, G.M.1
  • 25
    • 0002365689 scopus 로고
    • 'The Euclid package'
    • Ed. Sayre, D., Clarendon Press, Oxford
    • Spek, A. L. 'The Euclid package'. In Computational Crystallography. Ed. Sayre, D., Clarendon Press, Oxford, 1982, p. 528.
    • (1982) In Computational Crystallography , pp. 528
    • Spek, A.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.