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Volumn 121, Issue 34, 1999, Pages 7778-7786

Total synthesis of (-)-FR901483

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID ETHYL ESTER; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; FR 901483; IMMUNOSUPPRESSIVE AGENT; ISOXAZOLIDINE DERIVATIVE; KETONE DERIVATIVE; LACTAM DERIVATIVE; METIROSINE METHYL ESTER; NATURAL PRODUCT; SPIRO COMPOUND; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG;

EID: 0033199676     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991160h     Document Type: Article
Times cited : (100)

References (29)
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    • For a review of asymmetric 1,3-dipolar cycloadditions, see: (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. (b) Frederickson, M. Tetrahedron 1997, 53, 403-425.
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    • For a review of asymmetric 1,3-dipolar cycloadditions, see: (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909. (b) Frederickson, M. Tetrahedron 1997, 53, 403-425.
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    • For other approaches to this ring system, see: (a) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391-1402. (b) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281.
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    • For other approaches to this ring system, see: (a) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391-1402. (b) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281.
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    • For a preliminary communication describing the application of this chemistry to the synthesis of desmethylamino FR901483, see: Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442-6443.
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    • note
    • X-ray crystallographic data have been deposited at the Cambridge Crystallographic Data Centre.
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    • For the synthesis of azabicyclo[3.3.1]nonanes or bicyclo[3.3.1]-nonanes by aldol reactions, see: (a) Kinney, W. A.; Crouse, G. D.; Paquette, L. A. J. Org. Chem. 1983, 48, 4986-5000. (b) Patir, S.; Rosenmund, P.; Götz, P. H. Heterocycles 1996, 43, 15-22. (c) Taylor, R. J. K.; Turner, S. M.; Horwell, D. C.; Howarth, O. W.; Mahon, M. F.; Molloy, K. C. J. Chem. Soc., Perkin Trans. 1 1990, 2145-2150.
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    • For the synthesis of azabicyclo[3.3.1]nonanes or bicyclo[3.3.1]- nonanes by aldol reactions, see: (a) Kinney, W. A.; Crouse, G. D.; Paquette, L. A. J. Org. Chem. 1983, 48, 4986-5000. (b) Patir, S.; Rosenmund, P.; Götz, P. H. Heterocycles 1996, 43, 15-22. (c) Taylor, R. J. K.; Turner, S. M.; Horwell, D. C.; Howarth, O. W.; Mahon, M. F.; Molloy, K. C. J. Chem. Soc., Perkin Trans. 1 1990, 2145-2150.
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    • The formation of diastereomeric ammonium salts by protonation of tertiary amines is well-known: (a) Glaser, R.; Peng, Q.-J.; Perlin, A. S. J. Org. Chem. 1988, 53, 2172-2180. (b) Glaser, R.; Charland, J.-P.; Michel, A. J. Chem. Soc., Perkin Trans. 2 1989, 1875-1880.
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    • The formation of diastereomeric ammonium salts by protonation of tertiary amines is well-known: (a) Glaser, R.; Peng, Q.-J.; Perlin, A. S. J. Org. Chem. 1988, 53, 2172-2180. (b) Glaser, R.; Charland, J.-P.; Michel, A. J. Chem. Soc., Perkin Trans. 2 1989, 1875-1880.
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    • note
    • 3 as reported. Private communication from Dr. Motohiro Hino, Fujisawa Research Laboratories.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.