메뉴 건너뛰기




Volumn 64, Issue 3, 1999, Pages 1042-1044

Synthesis of the 16α,17α,21-trimethyl corticosteroid rimexolone from prednisolone

Author keywords

[No Author keywords available]

Indexed keywords

16ALPHA,17ALPHA,21 TRIMETHYLCORTICOSTEROID; DEXAMETHASONE; IODIDE; PREDNISOLONE; PREDNISOLONE TRIACETATE; RIMEXOLONE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG;

EID: 0033524880     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981848x     Document Type: Article
Times cited : (10)

References (43)
  • 1
    • 0344459695 scopus 로고    scopus 로고
    • U.S. Patent 4,686,214
    • (a) Boltralik, J. J. U.S. Patent 4,686,214.
    • Boltralik, J.J.1
  • 4
    • 0344459693 scopus 로고    scopus 로고
    • (d) Drugs Future 1997, 22, 1177.
    • (1997) Drugs Future , vol.22 , pp. 1177
  • 6
    • 0344028579 scopus 로고
    • Maryanoff, B. E., Maryanoff, C. A., Eds.; JAI Press: Greenwich, CT
    • (a) Livingston, D. A. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. A., Eds.; JAI Press: Greenwich, CT, 1992; Vol. 1, pp 137-174.
    • (1992) Advances in Medicinal Chemistry , vol.1 , pp. 137-174
    • Livingston, D.A.1
  • 14
    • 0344028580 scopus 로고    scopus 로고
    • European Patent 464,153 B1
    • (b) Pearlman, B. A. European Patent 464,153 B1.
    • Pearlman, B.A.1
  • 19
    • 0344891506 scopus 로고
    • (a) Kövendi, A.; Bodor, A.; Deésy, A.; Breazu, D. Rev. Chim. (Bucharest) 1976, 27, 467; Chem. Abstr. 1977, 86, 29990.
    • (1977) Chem. Abstr. , vol.86 , pp. 29990
  • 26
    • 0008672372 scopus 로고
    • 13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)- furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
    • (1986) Synthesis , pp. 921
    • Guntrum, E.1    Kuhn, W.2    Spönlein, W.3    Jäger, V.4
  • 27
    • 0008875421 scopus 로고
    • 13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)- furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
    • (1986) J. Org. Chem. , vol.51 , pp. 2525
    • Sampson, P.1    Roussis, V.2    Drtina, G.J.3    Koerwitz, F.L.4    Wiemer, D.F.5
  • 28
    • 0021950412 scopus 로고
    • 13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)- furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
    • (1985) J. Med. Chem. , vol.28 , pp. 428
    • Kamata, S.1    Haga, N.2    Mitsugi, T.3    Kondo, E.4    Nagata, W.5    Nakamura, M.6    Miyata, K.7    Odaguchi, K.8    Shimizu, T.9    Kawabata, T.10    Suzuki, T.11    Ishibashi, M.12    Yamada, F.13
  • 29
    • 0016798515 scopus 로고
    • 13C NMR spectrum of 13 (δ 120 (CH), 168, 171) is consistent with the 2(5H)-furanone (butenolide) structure, not the 3(2H)-furanone: Guntrum, E.; Kuhn, W.; Spönlein, W.; Jäger, V. Synthesis 1986, 921. Sampson, P.; Roussis, V.; Drtina, G. J.; Koerwitz, F. L.; Wiemer, D. F. J. Org. Chem. 1986, 51, 2525. For the synthesis of steroidal spirobutenolides of opposite C-17 configuration, see: Kamata, S.; Haga, N.; Mitsugi, T.; Kondo, E.; Nagata, W.; Nakamura, M.; Miyata, K.; Odaguchi, K.; Shimizu, T.; Kawabata, T.; Suzuki, T.; Ishibashi, M.; Yamada, F. J. Med. Chem. 1985, 28, 428. For steroidal 3(2H)-furanones, see: Gupta, P. K.; Jones, J. G. Ll.; Caspi, E. J. Org. Chem. 1975, 40, 1420.
    • (1975) J. Org. Chem. , vol.40 , pp. 1420
    • Gupta, P.K.1    Jones, J.G.Ll.2    Caspi, E.3
  • 31
    • 0344891505 scopus 로고    scopus 로고
    • note
    • Two examples of A → B type alkylation in the presence of the A-ring dienone have been recorded: 24 → 25 in ref 2 (30% yield); Example 19 in U.S. Patent 3,862,194 (yield unspecified).
  • 40
    • 0344459684 scopus 로고    scopus 로고
    • European Patent 608,178 A1
    • (e) Roussel, P.; Vivat, M. European Patent 608,178 A1.
    • Roussel, P.1    Vivat, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.