A novel radical-based synthesis of valerolactones

Synthetic Communications

Volumn 26, Issue 21, 1996, Pages 4039-4048

  Byers, Jeffrey H ^a   O'Leary, Brendan M ^a   Zraly, Maggie A ^a  

^a MIDDLEBURY COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; UNCLASSIFIED DRUG; VALEROLACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029750180     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003825     Document Type: Article

References (21)

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2. (b) Byers, J. H.; Lane, G.C. J. Org. Chem. 1993, 58, 3355.
3. (a) Byers, J. H.; Gleason, T. G.; Knight, K. S. Chem. Commun. 1991, 355.
4. (b) Byers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 33, 6953.
5. (c) Curran, D. P.; Thoma, G. J. J. Am. Chem. Soc. 1992, 114, 4436.
6. (d) Back, T. G.; Gladstone, P. L. Synlett 1993, 699.
7. (e) Renaud, P.; Vionnet, J. P. J. Org. Chem. 1993, 58, 5895.
8. (f) Curran, D. P.; Martin-Esker, A. A.; Ko, S. -B.; Newcomb, M. J. Org. Chem. 1993, 58, 4691.
9. (g) Renaud, P.; Vionnet, J. P. Chimia 1994, 48, 471.
10. (g) Vionnet, J. P.; Renaud, P. Helvetica Chimica Acta 1994, 77, 1781.
11. (h) Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
12. (i) Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
13. (j) Renaud, P.; Abazi, S. Synthesis, 1996, 253.
14. (a) Surzur, J. M.; Teissier, P. Bull. Chim. Soc. Fr. 1970, 653.
15. (b) Surzur, J. M.; Teissier, P. Bull. Chim. Soc. Fr. 1970, 1611.
16. Several recently published books describe organoselenium chemistry in general, with many examples of transformations of the phenylseleno group:
17. (a) Paulmier, C. "Selenium Reagents and Intermediates in Organic Synthesis," Pergamon, Oxford, 1986.
18. (b) Krief, A.; Hevesi, L. "Organoselenium Chemistry I," Springer: Berlin, 1988.
19. (c) "Organoselenium Chemistry," Liotta, D. Ed., Wiley, New York, 1987.
20. (d) "The Chemistry of Organoselenium and Tellurium Compounds," Patai, S.; Rappaport, Z., Eds., Wiley, New York, 1986.
21. Our synthesis of 1b was adapted from a procedure for the analogous ethyl diester described in ref 2f, substituting dimethyl methylmalonate for diethyl methylmalonate.