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Volumn 5, Issue 12, 1999, Pages 3651-3665

Studies towards trichodimerol: Novel cascade reactions and polycyclic frameworks

Author keywords

Aldol reactions; Biosynthesis; Cascade reactions; Natural products; Silyl enol ether

Indexed keywords

DEMETHYLTRICHODEMEROL; NATURAL PRODUCT; SILANE DERIVATIVE; SORBICILLIN; TRICHODIMEROL; UNCLASSIFIED DRUG;

EID: 0032761924     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19991203)5:12<3651::aid-chem3651>3.0.co;2-y     Document Type: Article
Times cited : (49)

References (71)
  • 1
    • 0000745211 scopus 로고
    • Trichodimerol (1) has been isolated independently from four different sources: a) R. Andrade, W. A. Ayer, P. P. Mebe, Can. J. Chem. 1992, 70, 2526-2535;
    • (1992) Can. J. Chem. , vol.70 , pp. 2526-2535
    • Andrade, R.1    Ayer, W.A.2    Mebe, P.P.3
  • 18
    • 0347583307 scopus 로고    scopus 로고
    • f) further general information available on the internet: http:// www.usatoday.com/life/health/lhs383.htm.
  • 21
    • 84855461241 scopus 로고
    • U. Schoellkopf, W. Hartwig, Angew. Chem. 1979, 91, 329-330; Angew. Chem. Int. Ed. Engl. 1979, 18, 310-311. R. J. thanks Dr. W. Hartwig, Bayer AG, Germany, for helpful discussions.
    • (1979) Angew. Chem. , vol.91 , pp. 329-330
    • Schoellkopf, U.1    Hartwig, W.2
  • 22
    • 84985502014 scopus 로고
    • R. J. thanks Dr. W. Hartwig, Bayer AG, Germany, for helpful discussions
    • U. Schoellkopf, W. Hartwig, Angew. Chem. 1979, 91, 329-330; Angew. Chem. Int. Ed. Engl. 1979, 18, 310-311. R. J. thanks Dr. W. Hartwig, Bayer AG, Germany, for helpful discussions.
    • (1979) Angew. Chem. Int. Ed. Engl. , vol.18 , pp. 310-311
  • 31
    • 0346952239 scopus 로고    scopus 로고
    • Purchased from Aldrich Chemical Co.
    • Purchased from Aldrich Chemical Co.
  • 42
    • 84990158080 scopus 로고
    • b) K. Weiniges, H. Iatridou, H.-G. Stammler, J. Weiss, Angew. Chem. 1989, 101, 485-486; Angew. Chem. Int. Ed. Engl. 1989, 28, 447-448.
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.28 , pp. 447-448
  • 43
    • 85087252921 scopus 로고    scopus 로고
    • note
    • 2O/AcOH).
  • 53
    • 33746494993 scopus 로고
    • 3N, see Y. Ito, T. Hirato, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013). Seagusa et al also observed partial silyl enol ether hydrolysis. In our case, the difference in steric environment apparently favors the dehydrosilylation of the more accessible side chain silyl enol ether while the more hindered cyclic enol ether undergoes acid-catalyzed hydrolysis. 44: Obtained from ketal ketone 32 by deprotonation with one equivalent of base (LiHMDS) under thermodynamic conditions, followed by quenching of the resulting enolate with the powerful electrophile PhSeCl. In this case the cyclic enolate is obviously the thermodynamically most stable species.
    • (1978) J. Org. Chem. , vol.43 , pp. 1011-1013
    • Ito, Y.1    Hirato, T.2    Saegusa, T.3
  • 59
    • 49249150992 scopus 로고
    • The direct 1,4-addition of TMSI to enone systems was previously reported: a) R. D. Miller, D. R. McKean, Tetrahedron Lett. 1979, 2305-2308;
    • (1979) Tetrahedron Lett. , pp. 2305-2308
    • Miller, R.D.1    McKean, D.R.2
  • 61
    • 0346952232 scopus 로고    scopus 로고
    • note
    • Attempts to remove the TMS protecting group by standard, fluoride-mediated procedures (e. g. HF-py, TBAF) resulted either in the decomposition of the starting material or in numerous polar products.
  • 64
    • 0347583289 scopus 로고    scopus 로고
    • note
    • During detailed studies we also isolated enol ether 55 as a byproduct (≈4%) from this reaction.
  • 65
    • 0031832945 scopus 로고    scopus 로고
    • and references therein
    • The Brønsted acid catalyzed thermal isomerization of silyl enol ethers was previously reported, see: A. Deyine, G. Dujardin, M. Mammeri, J.-M. Poirier, Synth. Commun. 1998, 28, 1817-1821, and references therein. In our case, the flask walls are apparently acidic enough at the high temperatures used to cause isomerization.
    • (1998) Synth. Commun. , vol.28 , pp. 1817-1821
    • Deyine, A.1    Dujardin, G.2    Mammeri, M.3    Poirier, J.-M.4
  • 67
    • 85087252886 scopus 로고    scopus 로고
    • note
    • 2, toluene and ether were obtained from Fischer Scientific.
  • 68
    • 85087252681 scopus 로고    scopus 로고
    • note
    • n (1.0 g) and phosphomolybdic acid (1.5 g).
  • 70
    • 0347583290 scopus 로고    scopus 로고
    • note
    • Alternatively, on a large scale, diketo dilactones 28a/b could be purified by trituration in warm ether.
  • 71
    • 0348212950 scopus 로고    scopus 로고
    • note
    • Caution: This reaction proved very scale-dependent and sensitive!


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.