The solid-phase combinatorial synthesis of β-thioketones

Tetrahedron

Volumn 53, Issue 19, 1997, Pages 6595-6609

  Chen, Chixu ^a   Ahlberg Randall, Lisa A ^a   Miller, R Bryan ^a   Jones, A Daniel ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIOKETONE;

CONFERENCE PAPER; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; PURIFICATION; REACTION ANALYSIS;

EID: 0030896376     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00219-6     Document Type: Conference Paper

References (18)

1. Chen, C.; Ahlberg Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661-2.
2. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-54.
3. Literature reviews: (a) Leznoff, C. C. Acc. Chem. Res. 1978, 11, 327.
4. (b) Leznoff, C. C. Chem. Soc. Rev. 1974, 3, 65.
5. Literature reviews: (a) Fréchet, J. M. J. Tetrahedron, 1981, 37, 663-83.
6. (b) Crowley, J. I.; Rapoport, H. Acc. Chem. Res., 1976, 9, 135-44.
7. Literature review: L.A. Thompson, J.A. Ellman, Chem. Rev. 1996, 96, 555.
8. Furka, A.; Sebestyen, F.; Asgedom, M.; Dibo, G. Int. J. Pept. Prot. Res. 1991, 37, 487-93.
9. (a) Frechet, J. M. J.; Nuyens, L. J. Can. J. Chem. 1976, 54, 926-34.
10. (b) Fyles, T. M.; Leznoff, C. C.; Weatherston, J. Can. J. Chem. 1978, 56, 1031-41.
11. For an example of effective site isolation, see: Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-2.
12. (a) See reference 7b.
13. (b) Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 935-42.
14. 3N/DMSO conditions resulted in acid-catalyzed deprotection of the trityl moiety, sulfur trioxide pyridine complex gave very satisfactory results: Parikh, J. R.; von E. Doering, W. J. Am. Chem. Soc. 1967, 89, 5505-7.
15. Frechet, J. M.; Schuerch, C. J. Am. Chem. Soc. 1971, 93, 492-6.
16. Stewart, J. M.; Young, J. D. Solid Phase Peptide Synthesis; W. H. Freeman and Co.: San Francisco, 1969, pp. 55.
17. After submission of the communication of these results, the use of GC to characterize the products of a combinatorial synthesis was reported: Ohlmeyer, M. H. J.; Swanson, R. N.; Dillard, L. W.; Reader, J. C.; Asouline, G.; Kobayashi, R.; Wigler, M.; Still, W. C. Proc. Natl. Acad. Sci, U.S.A. 1993, 90, 10922-6.
18. For a recent example of this strategy, see: Kurth, M. J.; Ahlberg Randall, L.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Kang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862-4