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Volumn 71, Issue 1, 2006, Pages 337-340

Oppolzer sultam directed aldol as a key step for the stereoselective syntheses of antitumor antibiotic belactosin C and its synthetic congeners

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; CATALYST SELECTIVITY; ISOMERS; ORGANIC ACIDS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

EID: 31144436305     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0516887     Document Type: Article
Times cited : (45)

References (29)
  • 11
    • 31144474766 scopus 로고    scopus 로고
    • note
    • The acyl-sultam prepared in two steps in overall yield 80%
  • 14
    • 31144473046 scopus 로고    scopus 로고
    • note
    • The major diastereomer 12a was crystallized as silyl ether. The minor distereomer 12b initially isolated as liquid but slowly it was crystallized out after a period of one month. The absolute stereochemistry 1′R,2R was assigned.
  • 20
    • 31144472059 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of crude product. Our attempt to obtain a crystal of 13 was not successful. The absolute stereochemistry was assigned by analogy of 12a.
  • 22
    • 31144462515 scopus 로고    scopus 로고
    • note
    • 13
  • 27
    • 31144451238 scopus 로고    scopus 로고
    • note
    • 2Cl/pyridine gave the product but in poor yields.
  • 28
    • 31144438279 scopus 로고    scopus 로고
    • note
    • For preparation of dipeptide 23, see the Supporting Information.
  • 29
    • 31144450424 scopus 로고    scopus 로고
    • note
    • Synthetic analogues 3, 4, and 24, which were intended to be applied for testing against cancer cell lines, were not deprotected; belactosin C itself has greater activity in protected form.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.