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Volumn 50, Issue 35, 2009, Pages 5050-5052

An efficient synthesis of oosporein

Author keywords

Diquinone; Oosporein; Thiele Winter acetoxylation; Total synthesis

Indexed keywords

ACETIC ACID DERIVATIVE; BENZOFURAN DERIVATIVE; CUPRIC ION; DRUG METABOLITE; ISOPHOENICIN; NATURAL PRODUCT; OOSPOREIN; PHOENICIN; PYRROLIDINE DERIVATIVE; QUINONE DERIVATIVE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67650087497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.103     Document Type: Article
Times cited : (19)

References (30)
  • 16
    • 67650008510 scopus 로고    scopus 로고
    • note
    • ® search failed to locate any newer syntheses of oosporein than the one described by Posternak in Ref. 9.
  • 18
    • 67650030218 scopus 로고    scopus 로고
    • note
    • 13
  • 21
    • 67650018604 scopus 로고    scopus 로고
    • note
    • More rapid isolation of the products (in approximately 80% yield) could be accomplished by removal of most of the methanol under reduced pressure, followed by dilution with water and isolation of the products by suction filtration. Failure to remove most of the methanol prior to dilution with water greatly diminished the yield of the product obtained.
  • 24
    • 0037218640 scopus 로고    scopus 로고
    • Mixtures of quinones and tertiary amines have been observed to form stable radical anion/radical cation pairs. See, for example:
    • Mixtures of quinones and tertiary amines have been observed to form stable radical anion/radical cation pairs. See, for example:. Dworniczak M. React. Kinet. Catal. Lett. 78 (2003) 65
    • (2003) React. Kinet. Catal. Lett. , vol.78 , pp. 65
    • Dworniczak, M.1
  • 25
    • 67650050428 scopus 로고    scopus 로고
    • note
    • The ratio of solvent volume to mixture weight (10 mL of methanol per gram of mixture) appeared to be more critical than the number of washings. For identical one gram samples, one trituration with 10 mL of methanol produced 2 in 45% yield, two triturations with 5 mL each of methanol produced 2 in 49% yield, and three triturations with 3 mL each of methanol produced 2 in 51% yield, all uncontaminated by 3.
  • 26
    • 67650013206 scopus 로고    scopus 로고
    • note
    • As yields for the conversion of 2 into 4 are quantitative, this modification, had it been successful, would have only resulted in a saving of time, not an improvement of yield.
  • 27
    • 67650059007 scopus 로고    scopus 로고
    • note
    • While 6 equiv of pyrrolidine (relative to diquinone) were sufficient for the conversion of 4 into 8, the conversion of 1 into 9 required 12 equiv of pyrrolidine. Use of lesser amounts of pyrrolidine led to contamination of 9 with an unidentified impurity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.