Studies on the synthesis of aureolic acid antibiotics: Acyloin glycosidation studies

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6098-6099

  Roush, William R ^a   Briner, Karin ^a   Kesler, Brenda S ^a   Murphy, Megan ^a   Gustin, Darin J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; OLIVOMYCIN;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029791485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960932e     Document Type: Article

References (16)

1. Remers, W. A.; Iyengar, B. S. In Cancer Chemotherapeutic Agents; Foye, W. O., Ed.; American Chemical Society: Washington, DC, 1995; p 578.
2. Leading references to the work of Weinreb, Franck, Thiem, Binkley, Crich, and Toshima, who have made important contributions to the synthesis of the aureolic acid antibiotics, are provided in ref 4.
3. Roush, W. R.; Murphy, M. J. Org. Chem. 1992, 57, 6622.
4. Roush, W. R.; Lin, X.-F. J. Am. Chem. Soc. 1995, 117, 2236 and references cited therein.
5. Sebesta, D. P.; Roush, W. R. J. Org. Chem. 1992, 57, 4799.
6. Thiem, J.; Gerken, M.; Snatzke, G. Liebigs Ann. Chem. 1983, 448.
7. Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960.
8. Grewal, G.; Kaila, N.; Franck, R. W. J. Org. Chem. 1992, 57, 2084.
9. Hashimoto, S.; Yanagiya, Y.; Honda, T.; Ikegami, S. Chem. Lett. 1992, 1511.
10. See footnote 4b in ref 7 and ref 7 in: Ramish, S.; Kaila, N.; Grewal, G.; Franck, R. W. J. Org. Chem. 1990, 55, 5.
11. Preuss, R.; Schmidt, R. R. Synthesis 1988, 694.
12. Miyamoto, M.; Morita, K.; Kawamatsu, Y.; Noguchi, S.; Marumoto, R.; Sasai, M.; Nohara, A.; Nakadaira, Y.; Lin, Y. Y.; Nakanishi, K. Tetrahedron 1966, 22, 2761.
13. 2.
14. Trisaccharide 12 with chloroacetate groups in the C and D residues was synthesized by using appropriate modifications of our published procedure (ref 5); details of the synthesis of 12 are provided in the Supporting Information. Acetate protecting groups in the C and D residues could not be removed selectively in the presence of the isobutyrate in the E residue.
15. Details of the synthesis of acyloin 14 are provided in the supporting information.
16. 2, -5 to 23°C, 4 A sieves) gave the β-trisaccharide conjugate in ca. 10% yield, while attempted glycosidations of 8 with 13 were unsuccessful.