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Volumn , Issue 2, 1996, Pages 297-304

Towards the Total Synthesis of Ambruticin: Preparation of the Fully Functionalised Right-Hand Portion Using the Intramolecular Silyl-Modified Sakurai (ISMS) Annulation

Author keywords

[No Author keywords available]

Indexed keywords

AMBRUTICIN;

EID: 0029921283     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4185     Document Type: Article
Times cited : (27)

References (47)
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    • Zeneca Fellow 1994-1997
    • Zeneca Fellow 1994-1997.
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    • Van der Plas, H.; Simonyi, M.; Aiderweireidt, F. C.; Lepoivre, J. A., Eds.; Elsevier: Amsterdam
    • (e) Sinaÿ, P., In Bio-organic Heterocycles, 1986; Synthesis, Mechanisms and Bioactivity; Van der Plas, H.; Simonyi, M.; Aiderweireidt, F. C.; Lepoivre, J. A., Eds.; Elsevier: Amsterdam, 1986, pp 59-74.
    • (1986) Bio-organic Heterocycles, 1986; Synthesis, Mechanisms and Bioactivity , pp. 59-74
    • Sinaÿ, P.1
  • 28
    • 4243893500 scopus 로고
    • For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 29
    • 33751157465 scopus 로고
    • For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
    • (1994) J. Org. Chem. , vol.59 , pp. 6161
    • Denmark, S.E.1    Coe, D.M.2    Pratt, N.E.3    Griedel, B.D.4
  • 30
    • 0001488391 scopus 로고
    • For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8467
    • Keck, G.E.1    Tarbet, K.H.2    Geraci, L.S.3
  • 31
    • 0023977798 scopus 로고
    • For an excellent review on homoallylic alcohol synthesis, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. For some selected pertinent references, see: (a) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161. (b) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467. (c) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1535
    • Brown, H.C.1    Jadhav, P.K.2    Bhat, K.S.3
  • 38
    • 0038180145 scopus 로고
    • Difficulties in substitution reactions in similar systems have previously been encountered. See for example: Holtz, H. D.; Stock, L. M. J. Am. Chem. Soc. 1965, 87, 2404.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 2404
    • Holtz, H.D.1    Stock, L.M.2
  • 39
    • 0012924040 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Trost, B. M.; Fleming, I., Eds.; Pergamon: London
    • For a review on the oxidation of carbon-halogen bonds, see: (a) Kilenyi, S. N. In Trost, B. M.; Fleming, I., Eds.; Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991; Vol. 7, p 653. Dave, P.; Byun, H-P.; Engel, R. Synth. Commun. 1986, 16, 1343.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 653
    • Kilenyi, S.N.1
  • 40
    • 0000018502 scopus 로고
    • For a review on the oxidation of carbon-halogen bonds, see: (a) Kilenyi, S. N. In Trost, B. M.; Fleming, I., Eds.; Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991; Vol. 7, p 653. Dave, P.; Byun, H-P.; Engel, R. Synth. Commun. 1986, 16, 1343.
    • (1986) Synth. Commun. , vol.16 , pp. 1343
    • Dave, P.1    Byun, H.-P.2    Engel, R.3
  • 42
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    • This sequence could involve inter-alia, the Pummerer rearrangement of sulfide 12 into an aldehyde followed by addition of MeMgI and oxidation of the resulting alcohol to the methyl ketone
    • This sequence could involve inter-alia, the Pummerer rearrangement of sulfide 12 into an aldehyde followed by addition of MeMgI and oxidation of the resulting alcohol to the methyl ketone.
  • 47
    • 1542716573 scopus 로고
    • Olefin 18 was initially transformed into the α-diol 21 in 67% yield using the Upjohn catalytic dihydroxylation protocol: Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1987, 1973. It is interesting to note that osmylation proceeds from the least hindered face of the dihydropyran substrate (Scheme 6). Benzoylation of 21, using p-bromobenzoyl chloride (pBBCl) in the presence of catalytic quantities of 4-dimethylamino pyridine, resulted in the preferential formation of the monobenzoylated material 22 accompanied by minor amounts of the bis-benzoylated compound 20. Although crystalline, 22 proved unsuitable for X-Ray analysis, the minor bis-benzoyl derivative 20 gave good quality X-Ray crystals.
    • (1987) Tetrahedron Lett.
    • Van Rheenen, V.1    Kelly, R.C.2    Cha, D.Y.3


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