Hydroximate as a synthetically useful functional group: A novel synthesis of lactones using hydroximates as a tether

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 229-232

  Miyata, Okiko ^a   Nishiguchi, Atsuko ^a   Ninomiya, Ichiya ^a   Naito, Takeaki ^a   Aœ, Keiichi ^b   Okamura, Kimio ^b  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030039673     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02135-3     Document Type: Article

References (13)

1. Neilson, D. G. The Chemistry of Amidines and Imidates; vol. 2, Patai, S.; Rappoport, Z. eds.; John Wiley and Sons, Inc.: Chichester, 1991; pp. 425-483.
2. 3, 3-Sigmatropic rearrangement of hydroximate has been previously reported as a method for synthesis of N-allylhydroxamic acid. De La Torre, J. A.; Fernandez, M.; Morgans, D.; Smith, Jr. D. B.; Talamas, F. X.; Trejo, A. Tetrahedron Lett. 1994, 35, 15-18.
3. We have reported thiyl radical addition-cyclization of dienylamides for lactam synthesis, (a) Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc. Perkin Trans. 1. 1995, 19-26;
4. (b) Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. Chem. Pharm. Bull. 1993, 41, 217-219.
5. Lactone syntheses by radical cyclization: (a) Walling, C.; Cooley, J. H.; Ponaras, A. A.; Racah, E. J. J. Am. Chem. Soc. 1966, 88, 5361-5363;
6. (b) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566;
7. Stork, G.; Mook, R.; Biller, Jr. S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742;
8. Belletire, J. L.; Mohmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363-4366;
9. (e) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750;
10. (f) Fukuzawa, S.; Tsuchimoto, T. SYNLETT. 1993, 803-804.
11. The substrates 4a-d, 7, and 10a-d were prepared according to the reported procedure; Johnson, J, E.; Springfield, J. R.; Hwang, J. S.; Hayes, L. J.; Cunningham, W. C.; McClaugherty, D. L. J. Org. Chem. 1971, 36, 284-294.
12. 3. Final R value was 0.060 for 5980 reflections.
13. This reaction condition has been developed as the methods of conversion of oxime ethers or hydrazones into ketones. Sakamoto, T.; Kikugawa, Y. Synthesis 1993, 563-564.