메뉴 건너뛰기




Volumn 28, Issue 21, 1998, Pages 4043-4057

Stereospecific synthesis of steroidal 20,16-γ-carbolactones

Author keywords

[No Author keywords available]

Indexed keywords

20,16 GAMMA CARBOLACTONE DERIVATIVE; ANDROSTANE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031658233     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004965     Document Type: Article
Times cited : (12)

References (24)
  • 2
    • 0004208435 scopus 로고
    • Reinhold Publishing Corp., New York, NY
    • Fieser, L. F.; Fieser, M. Steroids, Reinhold Publishing Corp., New York, NY (1959), p 810-846. Basu, N. and Rastogi, R. P. Phytochemistry 1967, 6, 1249. Shakirov, R. and Yunusov, M. S. Nat. Prod. Rep. 1990, 7, 557. Kessar, S.V.; Rampal, A.L. and Gupta, Y.P. Tetrahedron 1968, 24, 905 and references cited therein.
    • (1959) Steroids , pp. 810-846
    • Fieser, L.F.1    Fieser, M.2
  • 3
    • 0001029133 scopus 로고
    • Fieser, L. F.; Fieser, M. Steroids, Reinhold Publishing Corp., New York, NY (1959), p 810-846. Basu, N. and Rastogi, R. P. Phytochemistry 1967, 6, 1249. Shakirov, R. and Yunusov, M. S. Nat. Prod. Rep. 1990, 7, 557. Kessar, S.V.; Rampal, A.L. and Gupta, Y.P. Tetrahedron 1968, 24, 905 and references cited therein.
    • (1967) Phytochemistry , vol.6 , pp. 1249
    • Basu, N.1    Rastogi, R.P.2
  • 4
    • 0009149181 scopus 로고
    • Fieser, L. F.; Fieser, M. Steroids, Reinhold Publishing Corp., New York, NY (1959), p 810-846. Basu, N. and Rastogi, R. P. Phytochemistry 1967, 6, 1249. Shakirov, R. and Yunusov, M. S. Nat. Prod. Rep. 1990, 7, 557. Kessar, S.V.; Rampal, A.L. and Gupta, Y.P. Tetrahedron 1968, 24, 905 and references cited therein.
    • (1990) Nat. Prod. Rep. , vol.7 , pp. 557
    • Shakirov, R.1    Yunusov, M.S.2
  • 5
    • 0014232885 scopus 로고
    • and references cited therein
    • Fieser, L. F.; Fieser, M. Steroids, Reinhold Publishing Corp., New York, NY (1959), p 810-846. Basu, N. and Rastogi, R. P. Phytochemistry 1967, 6, 1249. Shakirov, R. and Yunusov, M. S. Nat. Prod. Rep. 1990, 7, 557. Kessar, S.V.; Rampal, A.L. and Gupta, Y.P. Tetrahedron 1968, 24, 905 and references cited therein.
    • (1968) Tetrahedron , vol.24 , pp. 905
    • Kessar, S.V.1    Rampal, A.L.2    Gupta, Y.P.3
  • 8
    • 85038540562 scopus 로고    scopus 로고
    • note
    • b. Epimerization of lactone 8 to 9 has been described in this reference.
  • 11
    • 0000399249 scopus 로고
    • Vespertilin (1b): González, A. G.; Francisco, C. G.; Barreira, R. F. and Lopez, E. S. An. Quím. 1971, 67, 433 (Chem. Abst. 1971, 75, 115890n). Solanolide (1c): Chakravarty, A. K.; Das, B. and Pakrashi, S. C. Phytochemistry 1982, 21, 2083. See also Lycopersiconolide: Nagaoka, T.; Yoshihara, T. and Sakamura, S. Phytochemistry 1987, 26, 2113, and 20S-hydroxyvespertilin: Gonzalez, A. G.; Freire, R.; Francisco, C. G.; Salazar, J. A. and Suárez, E. Tetrahedron 1973, 29, 1731.
    • (1971) An. Quím. , vol.67 , pp. 433
    • González, A.G.1    Francisco, C.G.2    Barreira, R.F.3    Lopez, E.S.4
  • 12
    • 85031207184 scopus 로고
    • Vespertilin (1b): González, A. G.; Francisco, C. G.; Barreira, R. F. and Lopez, E. S. An. Quím. 1971, 67, 433 (Chem. Abst. 1971, 75, 115890n). Solanolide (1c): Chakravarty, A. K.; Das, B. and Pakrashi, S. C. Phytochemistry 1982, 21, 2083. See also Lycopersiconolide: Nagaoka, T.; Yoshihara, T. and Sakamura, S. Phytochemistry 1987, 26, 2113, and 20S-hydroxyvespertilin: Gonzalez, A. G.; Freire, R.; Francisco, C. G.; Salazar, J. A. and Suárez, E. Tetrahedron 1973, 29, 1731.
    • (1971) Chem. Abst. , vol.75
  • 13
    • 0001438835 scopus 로고
    • Vespertilin (1b): González, A. G.; Francisco, C. G.; Barreira, R. F. and Lopez, E. S. An. Quím. 1971, 67, 433 (Chem. Abst. 1971, 75, 115890n). Solanolide (1c): Chakravarty, A. K.; Das, B. and Pakrashi, S. C. Phytochemistry 1982, 21, 2083. See also Lycopersiconolide: Nagaoka, T.; Yoshihara, T. and Sakamura, S. Phytochemistry 1987, 26, 2113, and 20S-hydroxyvespertilin: Gonzalez, A. G.; Freire, R.; Francisco, C. G.; Salazar, J. A. and Suárez, E. Tetrahedron 1973, 29, 1731.
    • (1982) Phytochemistry , vol.21 , pp. 2083
    • Chakravarty, A.K.1    Das, B.2    Pakrashi, S.C.3
  • 14
    • 0000308073 scopus 로고
    • Vespertilin (1b): González, A. G.; Francisco, C. G.; Barreira, R. F. and Lopez, E. S. An. Quím. 1971, 67, 433 (Chem. Abst. 1971, 75, 115890n). Solanolide (1c): Chakravarty, A. K.; Das, B. and Pakrashi, S. C. Phytochemistry 1982, 21, 2083. See also Lycopersiconolide: Nagaoka, T.; Yoshihara, T. and Sakamura, S. Phytochemistry 1987, 26, 2113, and 20S-hydroxyvespertilin: Gonzalez, A. G.; Freire, R.; Francisco, C. G.; Salazar, J. A. and Suárez, E. Tetrahedron 1973, 29, 1731.
    • (1987) Phytochemistry , vol.26 , pp. 2113
    • Nagaoka, T.1    Yoshihara, T.2    Sakamura, S.3
  • 15
    • 0012772887 scopus 로고
    • Vespertilin (1b): González, A. G.; Francisco, C. G.; Barreira, R. F. and Lopez, E. S. An. Quím. 1971, 67, 433 (Chem. Abst. 1971, 75, 115890n). Solanolide (1c): Chakravarty, A. K.; Das, B. and Pakrashi, S. C. Phytochemistry 1982, 21, 2083. See also Lycopersiconolide: Nagaoka, T.; Yoshihara, T. and Sakamura, S. Phytochemistry 1987, 26, 2113, and 20S-hydroxyvespertilin: Gonzalez, A. G.; Freire, R.; Francisco, C. G.; Salazar, J. A. and Suárez, E. Tetrahedron 1973, 29, 1731.
    • (1973) Tetrahedron , vol.29 , pp. 1731
    • Gonzalez, A.G.1    Freire, R.2    Francisco, C.G.3    Salazar, J.A.4    Suárez, E.5
  • 16
    • 0013521646 scopus 로고
    • Addition reaction of the enolate of methyl propionate or propionic acid to the C-17 keto group does not proceed as cleanly as with the t-butyl propionate enolate. Doller, D. and Gros, E. G. Synth. Commun. 1990, 20, 3115.
    • (1990) Synth. Commun. , vol.20 , pp. 3115
    • Doller, D.1    Gros, E.G.2
  • 17
    • 0001116524 scopus 로고
    • Schnuff, N. R. and Trost, B. M. J. Org. Chem. 1983, 48, 1404. For assignment of Z stereochemistry, see: Kobayashi, N.; Hisada, A. and Shimada, K. J. Chem. Soc. Perkin Trans. I, 1993, 31.
    • (1983) J. Org. Chem. , vol.48 , pp. 1404
    • Schnuff, N.R.1    Trost, B.M.2
  • 23
    • 85038540575 scopus 로고    scopus 로고
    • note
    • 15 which afforded the corresponding nitrile analog to 15. The remaining steps were as described for the 3β-OTBDMS steroid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.