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Volumn 5, Issue 12, 2003, Pages 2095-2098

Synthetic studies on ecteinascidin-743: Constructing a versatile pentacyclic intermediate for the synthesis of ecteinascidins and saframycins

Author keywords

[No Author keywords available]

Indexed keywords

ECTEINASCIDIN 743; SAFRAMYCIN A; SAFRAMYCIN B; TETRAHYDROISOQUINOLINE DERIVATIVE;

EID: 0141519496     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034575n     Document Type: Article
Times cited : (52)

References (31)
  • 5
    • 0000693545 scopus 로고    scopus 로고
    • Ecteinacidin-743 in taxane/Antracycline pretreated advanced/metastatic breast cancer patients: Preliminary results with the 24 h continuous infusion Q3 week schedule
    • New Orleans, May 20-23; Abstract number 592
    • (a) Zelek, L.; Yovine, A.; Etienne, B.; Jimeno, J.; Taamma, A.; Martín, C.; Spielmann, M.; Cvitkovic, E.; Misset, J. L. Ecteinacidin-743 in taxane/Antracycline pretreated advanced/metastatic breast cancer patients: preliminary results with the 24 h continuous infusion Q3 week schedule, presented at the American Society of Clinical Oncology, 36th Annual Meeting, New Orleans, May 20-23, 2000; Abstract number 592.
    • (2000) American Society of Clinical Oncology, 36th Annual Meeting
    • Zelek, L.1    Yovine, A.2    Etienne, B.3    Jimeno, J.4    Taamma, A.5    Martín, C.6    Spielmann, M.7    Cvitkovic, E.8    Misset, J.L.9
  • 26
    • 0141553192 scopus 로고    scopus 로고
    • note
    • It should be noted that the free phenol was found to be essential for a successful Pictet-Spengler cyclization reaction to proceed. Related substrates containing the methylenedioxy moiety or simple aryl methyl ethers failed to afford the corresponding Pictet-Spengler products.
  • 27
    • 0141441670 scopus 로고    scopus 로고
    • note
    • 1H NMR data of the pre-Pictet-Spengler β-lactam used to prepare i to that of 21 was used to establish the relative stereochemistry of 21.
  • 28
    • 0141664679 scopus 로고    scopus 로고
    • note
    • The coupling with the acid chloride 18 in the presence of DMAP did not lead to detectable racemization.
  • 29
    • 0000913103 scopus 로고
    • A search of the literature did not reveal any general methods for the reduction of β-lactams to aldehydes. For a pertinent reference, see: Ojima, I.; Zhao, M.; Yamato, T.; Nakahashi, K.; Yamashita, M.; Abe, R. J. Org. Chem. 1991, 56, 5263-5277.
    • (1991) J. Org. Chem. , vol.56 , pp. 5263-5277
    • Ojima, I.1    Zhao, M.2    Yamato, T.3    Nakahashi, K.4    Yamashita, M.5    Abe, R.6
  • 30
    • 0141776581 scopus 로고    scopus 로고
    • note
    • 1H NMR nOe studies.
  • 31
    • 0141776580 scopus 로고    scopus 로고
    • note
    • All new compounds gave satisfactory spectroscopic and analytical data consistent with the assigned structures (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.