The first syntheses of the 1-oxo-2-oxa-5-azaspiro[3.4]octane ring system found in oxazolomycin

Organic Letters

Volumn 2, Issue 14, 2000, Pages 1987-1990

  Papillon, Julien P N ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 OXO 2 OXA 5 AZASPIRO(3.4)OCTANE; 1-OXO-2-OXA-5-AZASPIRO(3.4)OCTANE; ANTIVIRUS AGENT; DIFFUSOMYCIN; LACTONE; OXAZOLE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; CONFORMATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTIVIRAL AGENTS; CRYSTALLOGRAPHY, X-RAY; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; OXAZOLES; OXIDATION-REDUCTION; SPIRO COMPOUNDS; STEREOISOMERISM; STREPTOMYCES;

EID: 0034644004     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0058792     Document Type: Article

References (22)

1. Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemara D. Tetrahedron Lett. 1985, 26, 1073-1076.
2. Kawazu, K.; Kanzaki, H.; Kawabata, G.; Kawai, S.; Kobayashi, A. Agric. Biol. Chem. 1989, 53, 1127-1133.
3. Tonew, E.; Tonew, M.; Gräfe, U.; Zöpel, P. Acta Virol. 1992, 36, 166-172.
4. (a) Ryu, G.; Hwang, S.; Kim, S. J. Antibiot. 1997, 50, 1064-1066.
5. (b) Ryu, G.; Kim, S. J. Antibot. 1999, 52, 193-197.
6. Kende, A. S.; Kawamura, K.; De Vita, R. J. J. Am. Chem. Soc. 1990, 112, 4070-4072.
7. Takahashi, K.; Kawabata, M.; Uemara, D. Tetrahedron Lett. 1985, 26, 1077-1078.
8. Hénaff, N.; Whiting, A. Org. Lett. 1999, 1, 1137-1139.
9. Corey, E. J.; Li, W.-D. Z.; Nagamitsu, T.; Fenteany, G. Tetrahedron 1999, 55, 3305-3316 and references therein.
10. See for example: Wedler, C.; Kunath, A.; Schick, H. J. Org. Chem. 1995, 60, 758-760.
11. Crystallographic data for 13 can be obtained on request from the Director, Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.
12. For an earlier account on the gem-substitution effect on β-lactone formation, see: Adam, W.; Encarnación, L. A. A. Chem Ber. 1982, 115, 2592-2605. See also: Jung, M. E. Synlett 1999, S1, 843-846 and references therein.
13. For an earlier account on the gem-substitution effect on β-lactone formation, see: Adam, W.; Encarnación, L. A. A. Chem Ber. 1982, 115, 2592-2605. See also: Jung, M. E. Synlett 1999, S1, 843-846 and references therein.
14. Linderman, R. J.; Suhr, Y. J. Org. Chem. 1988, 53, 1569-1572.
15. Pan, M.; Benneche, T. Synth. Commun. 1998, 1415-1419.
16. Reaction of N-benzyl proline methyl ester with acetone was then carried out to check the importance of the activated ester in this reaction. It gave the alkylated uncyclised product in 70% yield.
17. Seebach, D.; Boes, M.; Naef, R.; Schweiser, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
18. Khalil, E. M.; Subasinghe, N. L.; Johnson R. L Tetrahedron Lett. 1996, 37, 3441-3444.
19. (a) Pansare, S. V.; Huyer, G.; Arnold, L. D.; Vederas, J. C. Org. Synth. 1991, 70, 1-9.
20. (b) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105-7109.
21. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
22. Carlsen, P. H. G.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.