Carbon-carbon bond formation from small- and medium-ring lactol acetates via radical and oxonium ion intermediates. Synthesis of (±)-laurenan

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7648-7649

  Rychnovsky, Scott D ^a   Dahanukar, Vilas H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LAURENAN; OXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

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

EID: 0029838260     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614349     Document Type: Article

References (25)

1. (a) Rychnovsky, S. D.; Zeller, S.; Skalitzky, D. J.; Griesgraber, G. J. Org. Chem. 1990, 55, 5550-5551.
2. (b) Rychnovsky, S. D.; Griesgraber, G. J. Org. Chem. 1992, 57, 1559-1563.
3. (c) Rychnovsky, S. D. Chem. Rev. 1995, 95, 2021-2040.
4. (a) Beau, J.-M.; Sinay, P. Tetrahedron Lett. 1985, 26, 6185-6188.
5. (b) Beau, J.-M.; Sinay, P. Tetrahedron Lett. 1985, 26, 6189-6192.
6. (c) Beau, J.-M.; Sinay, P. Tetrahedron Lett. 1985, 26, 6193-6196.
7. Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, FL, 1995.
8. Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Exeter, 1995.
9. (a) Malatesta, V.; McKelvey, R. D.; Babcock, B. W.; Ingold, K. U. J. Org. Chem. 1979, 44, 1872-1873.
10. (b) Gregory, A. R.; Malatesta, V. J. Org. Chem. 1980, 45, 122-125.
11. Rychnovsky, S. D.; Powers, J. P.; LePage, T. J. J. Am. Chem. Soc. 1992, 114, 8375-8384.
12. See the transformation of compound 38 to 37 in: Ireland, R. E.; Norbeck, D. W.; Mandel, G. J. Am. Chem. Soc. 1985, 107, 3285-94.
13. Rychnovsky, S. D.; Dahanukar, V. H. Tetrahedron Lett. 1996, 37, 339-342.
14. Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Kim, B. H.; Ogilive, W. W.; Yiannikouros, G.; Prasad, C. V. C.; Veale, C. A.; Hark, R. R. J. Am. Chem. Soc. 1990, 112, 6263-6276.
15. Lactones 1c and 1d were prepared by alkylation of the N,N-dimethyl hydrazone of either cyclohexanone or cycloheptanone with 1-iodopentane, followed by hydrolysis and Baeyer-Villager oxidation (m-CPBA). (See the supporting information and ref 13a.)
16. Dahanukar, V. H.; Rychnovsky, S. D. J. Org. Chem., in press.
17. (a) Heras, F. G.; Resa-Fernández, P. J. Chem. Soc., Perkin Trans. 1 1982, 903-907.
18. (b) Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M., Shishiyama, Y.; Obayashi, M.; Nozaki, H. Tetrahedron 1983, 39, 967-973.
19. 13C-NMR correlation. (a) Carling, R. W.; Clark, S. J.; Holmes, A. B. J. Chem. Soc., Perkin Trans. 1 1992, 83-94.
20. (b) Kotsuki, H. Synlett 1992, 97-106.
21. Carling R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 565-567 and ref 13a.
22. Cyclic cyanohydrin 7 was prepared by the same procedure outlined in Scheme 1. The synthesis is presented in the supporting information.
23. Cyanohydrins 8 were isolated as a 3.6:1 mixture, but the configurations were not determined.
24. 2 (16%), hexanes (83%), and tert-butyl methyl ether (1%) as the eluent.
25. Nicolaou, K. C.; Hwang, C.-K.; Nugiel, D. A. J. Am. Chem. Soc. 1989, 111, 4136-4137.