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Volumn 40, Issue 35, 1999, Pages 6377-6381

Synthesis of the trans-syn-trans perhydrobenz[e]indene moiety of the stellettins and of the stelliferins

Author keywords

Cyclopropanation; Ene reaction; Terpenes; Trimethylsilyl halide

Indexed keywords

STELLETTIN DERIVATIVE; STELLIFERIN DERIVATIVE; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033609843     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01240-X     Document Type: Article
Times cited : (15)

References (47)
  • 23
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    • NaH, THF, rt: 48% yield, 9βH/9αH=4/1 conditions
    • (a) NaH, THF, rt: 48% yield, 9βH/9αH=4/1 (conditions: Clark, R. D.; Kozar, L. G.; Heathcock, C. H. Synth. Commun. 1975, 5, 1-5);
    • (1975) Synth. Commun. , vol.5 , pp. 1-5
    • Clark, R.D.1    Kozar, L.G.2    Heathcock, C.H.3
  • 24
    • 0000376544 scopus 로고
    • 3, THF, rt: 50% yield, 9βH/9αH=1/1 conditions
    • 3, THF, rt: 50% yield, 9βH/9αH=1/1 (conditions: Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429-6431);
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6429-6431
    • Corey, E.J.1    Virgil, S.C.2
  • 25
    • 0009600221 scopus 로고    scopus 로고
    • 3, toluene, 110°C: 31% yield, 9βH/9αH=1/1.
    • 3, toluene, 110°C: 31% yield, 9βH/9αH=1/1.
  • 28
    • 0009635060 scopus 로고    scopus 로고
    • note
    • 3) δ 16.6; 17.4; 21.8; 22.6; 23.7; 29.1; 33.6; 34.8; 35.5; 35.9; 39.1; 43.6; 48.6; 51.9; 57.8; 59.6; 88.4; 215.6.
  • 29
    • 0009578884 scopus 로고    scopus 로고
    • Prepared in the same way as 5. A methyl ether was introduced at C-3 because the TBS ether of aldehyde 5 was not stable under the acidic conditions of the ene cyclisation
    • Prepared in the same way as 5. A methyl ether was introduced at C-3 because the TBS ether of aldehyde 5 was not stable under the acidic conditions of the ene cyclisation.
  • 32
    • 0009650694 scopus 로고    scopus 로고
    • The reaction time (25 min) is critical since longer reaction times result in epimerisation at C-9
    • The reaction time (25 min) is critical since longer reaction times result in epimerisation at C-9.
  • 34
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    • In comprehensive organic synthesis
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • Snider, B. B. In comprehensive organic synthesis; Trost, B. M., Fleming, I., Eds.; The Prins and Carbonyl Ene Reactions. Pergamon: Oxford, 1991; Vol. 2, pp. 527-561.
    • (1991) The Prins and Carbonyl Ene Reactions , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 37
    • 0009580271 scopus 로고    scopus 로고
    • Crystallographic data for 12 and 15 have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk
    • Crystallographic data for 12 and 15 have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk
  • 41
    • 0000243233 scopus 로고    scopus 로고
    • Attempts to cyclopropanate with samarium amalgam resulted here in the transformation of the cyclopentenol into a cyclopentadiene.
    • Attempts to cyclopropanate with samarium amalgam (Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525-3532) resulted here in the transformation of the cyclopentenol into a cyclopentadiene.
    • J. Org. Chem. 1989 , vol.54 , pp. 3525-3532
    • Molander, G.A.1    Harring, L.S.2
  • 42
    • 0009642196 scopus 로고
    • The introduction of an angular methyl by directed cyclopropanation, oxidation, and dissolving metal reduction has been described earlier
    • The introduction of an angular methyl by directed cyclopropanation, oxidation, and dissolving metal reduction has been described earlier: Packer, R. A.; Whitehurst, J. S. J. Chem. Soc., Chem. Commun. 1975, 757-758.
    • (1975) J. Chem. Soc., Chem. Commun. , pp. 757-758
    • Packer, R.A.1    Whitehurst, J.S.2
  • 44
    • 0009650695 scopus 로고    scopus 로고
    • 3) δ 0.80 (s, 3H); 1.00 (s, 3H); 1.01 (s, 3H); 1.14 (s, 3H); 2.73 (dd, J=5.0, 10.9 Hz, 1H); 3.37 (s, 3H)
    • 3) δ 0.80 (s, 3H); 1.00 (s, 3H); 1.01 (s, 3H); 1.14 (s, 3H); 2.73 (dd, J=5.0, 10.9 Hz, 1H); 3.37 (s, 3H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.