Synthesis of liverwort sesquiterpene (-)-isocuparene (herbertene) via a Diels-Alder reaction using phenylethylamine as chiral auxiliary

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2731-2738

  Tori, Motoo ^a   Miyake, Takahiro ^a   Hamaguchi, Tomonobu ^a   Sono, Masakazu ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCUPARENE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030922874     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00313-3     Document Type: Article

References (23)

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13. Banerjee, A. K.; Pena-Matheud, C. A.; de Carrasco, M. C., J. Chem. Soc., Perkin Trans. 1., 1988, 2485; Ishibashi, H.; Nakatani, H.; Choi, D. J.; Taguchi, M.; Ikeda, M., Chem. Pharm. Bull., 1990, 38, 1738; Takano, S.; Moriya, M.; Ogasawara, K., Tetrahedron Lett., 1992, 33, 329; Saha, A. K.; Das, S.; Mukherjee, D., Tetrahedron Lett., 1994, 35, 3353; Ho, T.-L.; Chang, M. H., Tetrahedron Lett., 1994, 55, 4819; Bailey, W. F.; Jiang, X.-L.; McLeod, C. E., J. Org. Chem., 1995, 60, 7791; Srikrishna, A.; Krishnan, K.; Venkateswarlu, S.; Kumar, P. P., J. Chem. Soc., Perkin Trans. 1, 1995, 2033; Schwarz, J. B.; Meyers, A. I., J. Org. Chem., 1995, 60, 6511; Abad, A.; Agulló, C.; Arnó, M.; Cunat, A. C.; García, M. T.; Zaragozá, R. J., J. Org. Chem., 1996, 61, 5916; Fukuyarna, Y.; Kiriyama, Y.; Kodama, M., Tetrahedron Lett., 1996, 37, 1261; Chavan, S. P.; Ravindranathan, T.; Patil, S. S.; Dhondge, V. D.; Dantale, S. W., Tetrahedron Lett., 1996, 37, 2629; and references cited therein.
14. Banerjee, A. K.; Pena-Matheud, C. A.; de Carrasco, M. C., J. Chem. Soc., Perkin Trans. 1., 1988, 2485; Ishibashi, H.; Nakatani, H.; Choi, D. J.; Taguchi, M.; Ikeda, M., Chem. Pharm. Bull., 1990, 38, 1738; Takano, S.; Moriya, M.; Ogasawara, K., Tetrahedron Lett., 1992, 33, 329; Saha, A. K.; Das, S.; Mukherjee, D., Tetrahedron Lett., 1994, 35, 3353; Ho, T.-L.; Chang, M. H., Tetrahedron Lett., 1994, 55, 4819; Bailey, W. F.; Jiang, X.-L.; McLeod, C. E., J. Org. Chem., 1995, 60, 7791; Srikrishna, A.; Krishnan, K.; Venkateswarlu, S.; Kumar, P. P., J. Chem. Soc., Perkin Trans. 1, 1995, 2033; Schwarz, J. B.; Meyers, A. I., J. Org. Chem., 1995, 60, 6511; Abad, A.; Agulló, C.; Arnó, M.; Cunat, A. C.; García, M. T.; Zaragozá, R. J., J. Org. Chem., 1996, 61, 5916; Fukuyarna, Y.; Kiriyama, Y.; Kodama, M., Tetrahedron Lett., 1996, 37, 1261; Chavan, S. P.; Ravindranathan, T.; Patil, S. S.; Dhondge, V. D.; Dantale, S. W., Tetrahedron Lett., 1996, 37, 2629; and references cited therein.
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16. Banerjee, A. K.; Pena-Matheud, C. A.; de Carrasco, M. C., J. Chem. Soc., Perkin Trans. 1., 1988, 2485; Ishibashi, H.; Nakatani, H.; Choi, D. J.; Taguchi, M.; Ikeda, M., Chem. Pharm. Bull., 1990, 38, 1738; Takano, S.; Moriya, M.; Ogasawara, K., Tetrahedron Lett., 1992, 33, 329; Saha, A. K.; Das, S.; Mukherjee, D., Tetrahedron Lett., 1994, 35, 3353; Ho, T.-L.; Chang, M. H., Tetrahedron Lett., 1994, 55, 4819; Bailey, W. F.; Jiang, X.-L.; McLeod, C. E., J. Org. Chem., 1995, 60, 7791; Srikrishna, A.; Krishnan, K.; Venkateswarlu, S.; Kumar, P. P., J. Chem. Soc., Perkin Trans. 1, 1995, 2033; Schwarz, J. B.; Meyers, A. I., J. Org. Chem., 1995, 60, 6511; Abad, A.; Agulló, C.; Arnó, M.; Cunat, A. C.; García, M. T.; Zaragozá, R. J., J. Org. Chem., 1996, 61, 5916; Fukuyarna, Y.; Kiriyama, Y.; Kodama, M., Tetrahedron Lett., 1996, 37, 1261; Chavan, S. P.; Ravindranathan, T.; Patil, S. S.; Dhondge, V. D.; Dantale, S. W., Tetrahedron Lett., 1996, 37, 2629; and references cited therein.
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18. Kan, T.; Ohfune, Y., Tetrahedron Lett., 1995, 36, 943.
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22. The yields for these two steps were unexpectedly low despite several trials. This is presumably due to steric hindrance at the C-11 position.
23. D=-25.3, did not correspond with 71% ee determined for compound 5. This is due to inseparable impurity present in the sample.