Synthesis of amicetose by three enantioselective methods

Tetrahedron Asymmetry

Volumn 9, Issue 2, 1998, Pages 203-212

  Noecker, Lincoln A ^a   Martino, Joseph A ^a   Foley, Paul J ^a   Rush, Diane M ^a   Giuliano, Robert M ^a   Villani Jr , Frank J ^b  

^a VILLANOVA UNIVERSITY   (United States)

^b JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMICETOSE; DEOXYSUGAR; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; DERIVATIZATION; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; GAS CHROMATOGRAPHY; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0032579307     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00631-9     Document Type: Article

References (24)

1. Stevens, C. L.; Nagarajan, K.; Haskell, T. H. J. Org. Chem. 1991, 27, 2991.
2. Arcamone, F.; Barbieri, W.; Franceschi, G.; Penco, S.; Vigevani, A. J. Am. Chem. Soc. 1973, 95, 2008; Arcamone, F.; Franceschi, G.; Gioia, B.; Penco, S.; Vigevani, A. J. Am. Chem. Soc. 1973, 95, 2009.
3. Arcamone, F.; Barbieri, W.; Franceschi, G.; Penco, S.; Vigevani, A. J. Am. Chem. Soc. 1973, 95, 2008; Arcamone, F.; Franceschi, G.; Gioia, B.; Penco, S.; Vigevani, A. J. Am. Chem. Soc. 1973, 95, 2009.
4. Stevens, C. L.; Blumbergs, P.; Wood, D. L. J. Am. Chem. Soc. 1964, 86, 3592.
5. Chiral syntheses of amicetose from carbohydrates and non-carbohydrates, and racemic syntheses are listed in: Catelani, G.; Colonna, F.; Rollin, P. Gazz. Chim. Ital. 1989, 119, 389. For more recent syntheses, see: Marco, J. L. Synth. Comm. 1989, 19, 485; Lajsic, S.; Miljkovic, D.; O. Cetkovic, G. Carbohydr. Res. 1992, 233, 261; Pedersen, C.; Jensen, H. S. Acta. Chem. Scand. 1994, 48, 222; Kirschning, A.; Hary, U.; Ries, M. Tetrahedron 1995, 51, 2297.
6. Chiral syntheses of amicetose from carbohydrates and non-carbohydrates, and racemic syntheses are listed in: Catelani, G.; Colonna, F.; Rollin, P. Gazz. Chim. Ital. 1989, 119, 389. For more recent syntheses, see: Marco, J. L. Synth. Comm. 1989, 19, 485; Lajsic, S.; Miljkovic, D.; O. Cetkovic, G. Carbohydr. Res. 1992, 233, 261; Pedersen, C.; Jensen, H. S. Acta. Chem. Scand. 1994, 48, 222; Kirschning, A.; Hary, U.; Ries, M. Tetrahedron 1995, 51, 2297.
7. Chiral syntheses of amicetose from carbohydrates and non-carbohydrates, and racemic syntheses are listed in: Catelani, G.; Colonna, F.; Rollin, P. Gazz. Chim. Ital. 1989, 119, 389. For more recent syntheses, see: Marco, J. L. Synth. Comm. 1989, 19, 485; Lajsic, S.; Miljkovic, D.; O. Cetkovic, G. Carbohydr. Res. 1992, 233, 261; Pedersen, C.; Jensen, H. S. Acta. Chem. Scand. 1994, 48, 222; Kirschning, A.; Hary, U.; Ries, M. Tetrahedron 1995, 51, 2297.
8. Chiral syntheses of amicetose from carbohydrates and non-carbohydrates, and racemic syntheses are listed in: Catelani, G.; Colonna, F.; Rollin, P. Gazz. Chim. Ital. 1989, 119, 389. For more recent syntheses, see: Marco, J. L. Synth. Comm. 1989, 19, 485; Lajsic, S.; Miljkovic, D.; O. Cetkovic, G. Carbohydr. Res. 1992, 233, 261; Pedersen, C.; Jensen, H. S. Acta. Chem. Scand. 1994, 48, 222; Kirschning, A.; Hary, U.; Ries, M. Tetrahedron 1995, 51, 2297.
9. Chiral syntheses of amicetose from carbohydrates and non-carbohydrates, and racemic syntheses are listed in: Catelani, G.; Colonna, F.; Rollin, P. Gazz. Chim. Ital. 1989, 119, 389. For more recent syntheses, see: Marco, J. L. Synth. Comm. 1989, 19, 485; Lajsic, S.; Miljkovic, D.; O. Cetkovic, G. Carbohydr. Res. 1992, 233, 261; Pedersen, C.; Jensen, H. S. Acta. Chem. Scand. 1994, 48, 222; Kirschning, A.; Hary, U.; Ries, M. Tetrahedron 1995, 51, 2297.
10. Berti, G.; Catelani, G.; Magi, S.; Monti, L. Gazz. Chim. Ital. 1980, 110, 173.
11. Catelani, G.; Colonna, F.; Rollin, P. Gazz. Chim. Ital. 1989, 119, 389.
12. Brown, H. C. in Asymmetric Synthesis, 2, Part A, Morrison, J. D., Ed., Academic Press, New York, 1983, pp. 1-44.
13. Brown, H. C.; Jadhav, P. K.; Mandal, A. K. J. Org. Chem. 1982, 47, 5074.
14. Brown, H. C.; Vara Prasad, J. V. N. J. Am. Chem. Soc. 1986, 108, 2049.
15. Brown, H. C.; Vara Prasad, J. V. N.; Gupta, A. K. J. Org. Chem. 1986, 51, 4269.
16. Pirkle, W. H.; Hoekstra, M. S. J. Org. Chem. 1974, 39, 3904.
17. Greenwald, R. B.; Pendri, A.; Bolikal, D. J. Org. Chem. 1995, 60, 331.
18. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier, Oxford, 1994.
19. Hanson, J. R. An Introduction to Biotransformations in Organic Chemistry; W. H. Freeman, New York, 1995.
20. Di Bussolo, V.; Catelani, G.; Mastrorilli, E.; Di Bugno, C.; Giorgi, R. Tetrahedron: Asymmetry, 1996, 7, 3585.
21. Lopez, R.; Montero, E.; Sanchez, F.; Canada, J.; Fernandez-Mayoralas, A. J. Org. Chem., 1994, 59, 7027.
22. Ciuffreda, P.; Colombo, D.; Ronchetti, F.; Toma, L. J. Org. Chem. 1990, 55, 4187.
23. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
24. Smith, C. W.; Norton, D. G.; Ballard, S. A. J. Am. Chem. Soc. 1951, 73, 5267.