Synthesis of the bicyclic core of the nucleoside antibiotic octosyl acid A

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2236-2241

  More, Jesse D ^a,b   Finney, Nathaniel S ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LOYOLA UNIVERSITY MARYLAND   (United States)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

6-ENDO SELENOETHERIFICATION; DIASTEREOSELECTIVE ACETYLIDE ADDITION; NUCLEOSIDE ANTIBIOTIC OCTOSYL ACID A; OCTOSYL ACID; PHENYL;

ACETYLATION; CARBOXYLIC ACIDS; ORGANIC ACIDS;

ANTIBIOTICS;

ANTIBIOTIC AGENT; BICYCLO COMPOUND; CARBOXYLIC ACID; NUCLEOSIDE; OCTOSYL ACID A; PHENYL GROUP; SELENIUM; UNCLASSIFIED DRUG; ZINC ACETYLIDE; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ETHERIFICATION; STEREOCHEMISTRY;

ANTI-BACTERIAL AGENTS; MOLECULAR CONFORMATION; NUCLEOSIDES; STEREOISOMERISM;

EID: 33645021251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052025s     Document Type: Article

References (30)

1. Knapp, S. Chem. Rev. 1995, 95, 1859-1876.
2. (a) Isono, K.; Crain, P. F.; McCloskey, J. A. J. Am. Chem. Soc. 1975, 97, 943-945.
3. (b) Sato, T.; Hirasawa, K.; Uzawa, J.; Inaba, T.; Isono, K. Tetrahedron Lett. 1976, 1687-1690.
4. Hanessian, S.; Marcotte, S.; Machaalani, R.; Huang, G. Org. Lett. 2003, 5, 4277-4280.
5. Sakata, K.; Sakurai, A.; Tamura, S. Agric. Biol. Chem. 1973, 37, 697-699.
6. (a) Danishefsky, S. J.; Hungate, R. J. Am. Chem. Soc. 1986, 108, 2486-2487.
7. (b) Hanessian, S.; Kloss, J.; Sugawara, T. J. Am. Chem. Soc. 1986, 108, 2758-2759.
8. Kozaki, S.; Sakanaka, O.; Yasuda, T.; Shimizu, T.; Ogawa, S.; Suami, T. J. Org. Chem. 1988, 53, 281-286.
9. For synthetic studies, see: (a) Anzai, K.; Saita, T. Bull. Chem. Soc. Jpn. 1977, 50, 169-174.
10. (b) Kim, K. S.; Szarek, W. A. Carbohydr. Res. 1982, 100, 169-176.
11. (c) Araki, Y.; Endo, T.; Arai, Y.; Tanjo, M.; Ishido, Y. Tetrahedron Lett. 1989, 30, 2829-2832.
12. (d) Malolanarasimhan, K. Ph.D. Dissertation, Rutgers University, New Brunswick, NJ, 2001.
13. More, J. D.; Finney, N. S. Synlett 2003, 1307-1310.
14. Frantz, D. E.; Fassler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373-381.
15. More, J. D. Ph.D. Dissertation, University of California, San Diego, La Jolla, CA, March, 2004.
16. For a review of electrophile-induced cyclizations, see: Frederickson, M.; Grigg, R. Org. Prep. Proced. Int. 1997, 29, 33-62.
17. Haraguchi, K.; Hosoe, M.; Tanaka, H.; Tsuruoka, S.; Kanmuri, K.; Miyasaka, T. Tetrahedron Lett. 1998, 39, 5517-5520.
18. Trost, B. M.; Brieden, W.; Baringhaus, K. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1335-1336.
19. El-Sayed, E.; Anand, N. K.; Carreira, E. M. Org. Lett. 2001, 3, 3017-3020.
20. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
21. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
22. (b) Djerassi, C.; Engle, R. R. J. Am. Chem. Soc. 1953, 75, 3838-3840.
23. (a) Nicolaou, K. C.; Roecker, A. J.; Monenschein, H.; Guntupalli, P.; Follman, M. Angew. Chem., Int. Ed. Engl. 2003, 42, 3637-3642.
24. (b) Boger, D. L.; Lee, R. J.; Bounandm, P.-Y.; Meier, P. J. Org. Chem. 2000, 65, 6770-6772.
25. (a) Nicolaou, K. C.; Magolda, R. L.; Sipio, W. J.; Barnette, W. E.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 3784-3793.
26. (b) Nicolaou, K. C.; Petasis, N. A. Selenium in Natural Products Synthesis; CIS, Inc.: Philadelphia, 1984.
27. Lipshutz, B. H.; Barton, J. C. J. Am. Chem. Soc. 1992, 114, 1084-1086.
28. (a) Ballestri, M.; Chatgilialoglu, C.; Clark, K. B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678-683.
29. (b) For a review, see: Studer, A.; Amrein, S. Synthesis 2002, 835-849.
30. Miranda, L. S. M.; Vasconcellos, M. L. A. A. Synthesis 2004, 1767-1770.