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Volumn 48, Issue 37, 1992, Pages 7899-7938

Total synthesis of the ionophore antibiotic CP-61,405 (routiennocin)

Author keywords

1 (2 trimethylsilylethoxymethyl) pyrrole; Ionophore; routiennocin; spiroketal; tetra n propyl ammonium perruthenate; tricarbonyliron complexes

Indexed keywords

ANTIBIOTIC AGENT; IONOPHORE; ROUTIENNOCIN; UNCLASSIFIED DRUG;

EID: 0026658420     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)80467-1     Document Type: Article
Times cited : (100)

References (60)
  • 1
    • 84918190500 scopus 로고    scopus 로고
    • CP-61,405 has been given the name Routiennocin to indicate its source of isolation from Streptomyces routienni.
  • 2
    • 84918190499 scopus 로고    scopus 로고
    • Celmer, W.D.; Cullen, W.P.; Maeda, H.; Tone, J. U.S. Patent 4,547,523.
  • 17
    • 0002478056 scopus 로고
    • Total Synthesis of the Carboxylic Acid Ionophore Antibiotic CP-61,405 (Routiennocin)
    • This work has previously been communicated:
    • (1992) Synlett , vol.5 , pp. 395
    • Kotecha1    Ley2    Mantegani3
  • 18
    • 85064407106 scopus 로고
    • Total Synthesis of the Carboxylic Acid lonophore Antibiotic CP-61,405 (Routiennocin): Preparation of the Inherent Spiroketal Unit via a Reverse Coupling Process
    • (1992) Synlett , vol.5 , pp. 399
    • Diez-Martin1    Kotecha2    Ley3    Menendez4
  • 23
    • 0010228328 scopus 로고
    • Natural product synthesis using π-allyltricarbonyliron lactone complexes: Synthesis of parasorbic acid, the carpenter bee pheromone and malyngolide
    • (1985) Journal of Organometallic Chemistry , vol.285 , pp. C12
    • Horton1    Ley2
  • 27
    • 0010640653 scopus 로고
    • Preparation of the (R)-MPTA ester derivative and subsequent n.m.r. analysis at 500MHz showed the optical purity to be 82%ee. The optical purity was improved by crystallisation. See
    • (1969) J. Org. Chem. , vol.34 , pp. 2543
    • Dale1    Dull2    Mosher3
  • 32
    • 33845375446 scopus 로고
    • Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranes
    • (1986) Journal of the American Chemical Society , vol.108 , pp. 5919
    • Bhat1    Brown2
  • 33
    • 0010640653 scopus 로고
    • Preparation of the (R)-MPTA ester derivative and subsequent n.m.r. analysis at 500MHz showed the optical purity to be 94%ee. See
    • (1969) J. Org. Chem. , vol.34 , pp. 2543
    • Dale1    Dull2    Mosher3
  • 45
    • 84918190497 scopus 로고    scopus 로고
    • All new compounds gave satisfactory spectroscopic, microanalytical and/or accurate mass data.
  • 46
    • 84989478646 scopus 로고
    • Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis
    • For a review, see
    • (1981) Synthesis , pp. 165
    • Mancuso1    Swern2
  • 47
    • 84918190496 scopus 로고    scopus 로고
    • Macromodel, the Batchminprogram and the associated documentation are available from W.C. Still, Columbia University, New York.
  • 48
    • 84918190495 scopus 로고    scopus 로고
    • We would like to thank Dr. D.J. Williams and Ms. A.M.Z. Slawin for x-ray structure determinations.
  • 60
    • 33845550463 scopus 로고
    • Prepared by azeotropic removal of water (5 times) from the commercially available trihydrate followed by heating at 35°C under high vacuum (12h). See also, and reference 13.
    • (1983) J. Org. Chem. , vol.48 , pp. 2112
    • Sharma1    Fry2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.