메뉴 건너뛰기




Volumn 117, Issue 12, 1995, Pages 3448-3467

Total Synthesis of the Polyether Antibiotic Lonomycin A (Emericid)

Author keywords

[No Author keywords available]

Indexed keywords

LONOMYCIN A;

EID: 0028937415     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00117a014     Document Type: Article
Times cited : (157)

References (83)
  • 1
    • 0003869642 scopus 로고
    • Polyether Antibiotics
    • For an excellent review of the chemistry and biology of this family of natural products Marcel Dekker: New York Vols. 1 and 2.
    • For an excellent review of the chemistry and biology of this family of natural products, see: Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2.
    • (1982)
    • Westley, J.W.1
  • 2
    • 0002564128 scopus 로고
    • For an important early review of this subject, see
    • For an important early review of this subject, see: Bartlett, P. A. Tetrahedron 1981, 36, 3–72.
    • (1981) Tetrahedron , vol.36 , pp. 3-72
    • Bartlett, P.A.1
  • 3
    • 0018425810 scopus 로고
    • The introduction of allylic strain concepts to the design of complex synthesis targets appeared in the Kishi monensin synthesis
    • The introduction of allylic strain concepts to the design of complex synthesis targets appeared in the Kishi monensin synthesis: (i) Schmid, G.; Fukuyama, T.; Akasaka, K.; Kishi, Y. J. Am. Chem. Soc. 1979, 101, 259–260.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 259-260
    • Schmid, G.1    Fukuyama, T.2    Akasaka, K.3    Kishi, Y.4
  • 6
    • 33645897192 scopus 로고
    • A review of aspects of this topic has appeared
    • (b) A review of aspects of this topic has appeared: Hoffmann, R. W. Chem. Rev. 1989, 89, 1841–1860.
    • (1989) Chem. Rev. , vol.89 , pp. 1841-1860
    • Hoffmann, R.W.1
  • 10
    • 0001010896 scopus 로고
    • For previous publications in ionophore synthesis from this laboratory, see the following. Calcimycin (A23187)
    • For previous publications in ionophore synthesis from this laboratory, see the following. (a) Calcimycin (A23187): Evans, D. A.; Sacks, C. E.; Kleschick, W. A.; Taber, T. R. J. Am. Chem. Soc. 1979, 101, 6789–6791.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6789-6791
    • Evans, D.A.1    Sacks, C.E.2    Kleschick, W.A.3    Taber, T.R.4
  • 25
    • 85022884754 scopus 로고
    • Taisho Pharmaceutical Co. Ltd. Jpn. Belg, Patent BE
    • 874687, Sep 10. 1978. 15 pp. AI JP Appl. 78/30187, Mar 16
    • Yamagishi, M.; Mizoue, K.; Mizutani, T.; Hara, H.; Omura, S.; Seto, H.; Otake, N., Taisho Pharmaceutical Co. Ltd. Jpn. Belg, Patent BE 874687, Sep 10. 1978. 15 pp. AI JP Appl. 78/30187, Mar 16, 1978.
    • (1978)
    • Yamagishi, M.1    Mizoue, K.2    Mizutani, T.3    Hara, H.4    Omura, S.5    Seto, H.6    Otake, N.7
  • 26
    • 85022798214 scopus 로고
    • Taisho Pharmaceutical Co., Ltd., Jpn. U. S. Patent
    • 4199515. Apr 22, 1980, 5 pp JP Appl. 78/30187, Mar 16
    • (b) Hara, H.; Mizoue, K.; Mizutani, T.; Omura, S.; Otake, N.; Seto, H.; Yamagishi, M., Taisho Pharmaceutical Co., Ltd., Jpn. U. S. Patent. 4199515. Apr 22, 1980, 5 pp JP Appl. 78/30187, Mar 16, 1978.
    • (1978)
    • Hara, H.1    Mizoue, K.2    Mizutani, T.3    Omura, S.4    Otake, N.5    Seto, H.6    Yamagishi, M.7
  • 27
    • 85022769265 scopus 로고
    • Taisho Pharmaceutical Co., Ltd., Jpn. Jpn. Kokai Tokkoyo Koho
    • JP 55/66584 [80/66584], May 20 JP Appl. or Pr. 78/140574, Nov 15, 1978.
    • Taisho Pharmaceutical Co., Ltd., Jpn. Jpn. Kokai Tokkoyo Koho JP 55/66584 [80/66584], May 20, 1980. 4 pp. JP Appl. or Pr. 78/140574, Nov 15, 1978.
    • (1980) , pp. 4
  • 36
    • 0025111330 scopus 로고
    • For a preliminary communication from this laboratory on this subject, see
    • For a preliminary communication from this laboratory on this subject, see: Evans, D. A.; Sheppard, G. S. J. Org. Chem. 1990, 55, 5192—5194.
    • (1990) J. Org. Chem. , vol.55 , pp. 5192-5194
    • Evans, D.A.1    Sheppard, G.S.2
  • 44
    • 84989478646 scopus 로고
    • Synthesis
    • Mancuso, A. J.; Swern, D. Synthesis 1981, 165 — 185.
    • (1981) , pp. 165-— 185
    • Mancuso, A.J.1    Swern, D.2
  • 45
    • 0001924336 scopus 로고
    • For a discussion of (Z) enolate additions to chiral α-substituted aldehydes
    • For a discussion of (Z) enolate additions to chiral α-substituted aldehydes, see:(a) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1–115.
    • (1982) Top. Stereochem. , vol.13 , pp. 1-115
    • Evans, D.A.1    Nelson, J.V.2    Taber, T.R.3
  • 51
  • 56
    • 0026584263 scopus 로고
    • Precedent for the stereochemical course of this reaction can be found in the following two studies
    • Precedent for the stereochemical course of this reaction can be found in the following two studies:(a) Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797-800.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 797-800
    • Paterson, I.1    Channon, J.A.2
  • 61
    • 0022578985 scopus 로고
    • This concept has been articulated and tested in several instances
    • This concept has been articulated and tested in several instances:(a) Still, W. C.; Romero, A. G. J. Am. Chem. Soc. 1986, 108, 2105–2106.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 2105-2106
    • Still, W.C.1    Romero, A.G.2
  • 71
    • 85066103748 scopus 로고
    • Synthesis
    • For a review of Claisen rearrangements
    • For a review of Claisen rearrangements, see: Bennett, G. B. Synthesis 1977, 589—606.
    • (1977) , pp. 589-606
    • Bennett, G.B.1
  • 73
    • 85077634689 scopus 로고
    • Synthesis
    • Mitsunobu, O. Synthesis 1981, 1—28.
    • (1981) , pp. 1-28
    • Mitsunobu, O.1
  • 75
    • 0038875419 scopus 로고
    • For an analogous acid-catalyzed epoxide cascade reaction
    • For an analogous acid-catalyzed epoxide cascade reaction, see: Paterson, I.; Boddy, I. Tetrahedron Lett. 1988, 29, 5301—5304.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5301-5304
    • Paterson, I.1    Boddy, I.2
  • 76
    • 0000458209 scopus 로고
    • For a general review of hydroxyl-directed reactions
    • For a general review of hydroxyl-directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307–1370.
    • (1993) Chem. Rev. , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 77
    • 0025907660 scopus 로고
    • For a recent example, see
    • For a recent example, see: Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017–3020.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3017-3020
    • Martin, S.F.1    Dodge, J.A.2
  • 78
    • 0001332620 scopus 로고
    • For a detailed discussion of chelate-controlled carbonyl addition
    • For a detailed discussion of chelate-controlled carbonyl addition, see: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778–1784.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1778-1784
    • Chen, X.1    Hortelano, E.R.2    Eliel, E.L.3    Frye, S.V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.