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Volumn 29, Issue 40, 1988, Pages 5143-5146

A highly stereocontrolled total synthesis of the polyether antibiotic salinomycin. Crucial role of the 40-metoxybenzyl; (mpm) protecting group for hydroxy functions

Author keywords

[No Author keywords available]

Indexed keywords

SALINOMYCIN;

EID: 0023767662     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)80703-0     Document Type: Article
Times cited : (15)

References (30)
  • 1
    • 84914296869 scopus 로고
    • Chiral synthesis of polyketide-derived natural products. 22. For part 21, see Tone, H.; Nishi, T.; Oikawa, Y.; Hikota, M.; Yonemitsu
    • (1988) O. J. Chem. Soc. Perkin 1 , pp. 0000
  • 18
    • 84914296868 scopus 로고    scopus 로고
    • 13 was a 3: 1 stereoisomeric mixture with respect to the C17 acetal position, and used for further reactions without any difficulty.
  • 19
    • 84914296867 scopus 로고    scopus 로고
    • The synthesis of 18 from D-glucose will be reported elsewhere soon.
  • 21
    • 0000000441 scopus 로고
    • Decarbonylation Reactions Using Transition Metal Compounds
    • (1969) Synthesis , vol.1 , pp. 157
    • Tsuji1    Ohno2
  • 25
    • 84914296865 scopus 로고    scopus 로고
    • Although the mixture was also converted to 1, the conversion after separation of 15a and 15b was advantageous because of easy characterization of intermediate products by means of NMR spectroscopy.
  • 26
    • 84914296864 scopus 로고    scopus 로고
    • LDA as a base was less effective.
  • 27
    • 84914296863 scopus 로고    scopus 로고
    • Salinamycin (1) itself also underwent the same interesting reaction. When 1 was mixed with DDQ in methylene chloride, an initially formed red colored solution faded slowly to form 29 in 50% yield probably via a charge transfer complex between electron-donative 1 and DDQ.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.