Enantiospecific synthesis of 8-O-methylthioswainsonine from a derivative of D-glucose

Tetrahedron Asymmetry

Volumn 7, Issue 9, 1996, Pages 2567-2575

  Izquierdo, Isidoro ^a   Plaza, Maria T ^a   Aragon F ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE; SWAINSONINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030250059     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00330-8     Document Type: Article

References (13)

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2. 2. Izquierdo Cubero, I; Plaza López-Espinosa, M. T.; Richardson, A. C.; Suárez Ortega M. D., Carbohydr. Res., 1993, 242, 109-118.
3. 3. a) Izquierdo Cubero, I; Plaza López-Espinosa, M. T.; Asenjo Asenjo, R.; Rodriguez Alonso, M., Tetrahedron: Asymmetry, 1995, 6, 1117-1122;
4. b) Izquierdo Cubero, I; Plaza López-Espinosa, M. T.; Ramírez Fernández, A.; Aragón, F., J. Heterocycl. Chem., 1996, 32, 1-4.
5. 4. Siriwardena, A. H.; Chiaroni, A.; Riche, C.; Gierson, D. S., J. Org. Chem., 1992, 57, 5661-5666.
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7. 6. Robertson, G. J.; Griffith, C. F., J. Chem. Soc., 1935, 1193-1201.
8. 7. Kunz, H.; Weißmüller, J., Liebigs Ann. Chem., 1984, 66-77.
9. 8. Urban, F. J.; Breitenbach, R.; Vincent, L. A., J. Org. Chem., 1990, 55, 3670-3672; Sinwardena, A. H.; Chiaroni, A.; Riche, C.; El-Daber, S.; Winchester, B.; Grierson, D. S., J. Chem. Soc. Chem. Commun., 1992, 1531-1533.
10. 8. Urban, F. J.; Breitenbach, R.; Vincent, L. A., J. Org. Chem., 1990, 55, 3670-3672; Sinwardena, A. H.; Chiaroni, A.; Riche, C.; El-Daber, S.; Winchester, B.; Grierson, D. S., J. Chem. Soc. Chem. Commun., 1992, 1531-1533.
11. 9. Computerized representation of the most stable conformation for 4S-and 4R-1, calculated with the TRIPOS force field.
12. 10. Clark, M.; Cramer III, R. D.; Van Opdenbosch, N., J. Comput. Chem., 1989, 10, 982.
13. 11. TRIPOS force field is implemented in the SYBYL 6.1 program, available from Tripos Inc. 1699 S. Hanley Road, St. Louis, Missouri 63144-2913, USA.