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Tetrahedron Letters
Volumn 34, Issue 26, 1993, Pages 4149-4152
A highly efficient route to taxotere by the β-Lactam Synthon Method
Author keywords

[No Author keywords available]
Indexed keywords

DOCETAXEL;
EID: 0027173282     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)60514-2     Document Type: Article
Times cited : (136)
References (20)
  • 15
  • 17
    • 84914363665 scopus 로고    scopus 로고
    • Kepler, J.A.; Taylor, G.F.; Thornton, S.S.; Wall, J.F.; Second National Cancer Institute Workshop on Taxol and Taxus, September 23-24, 1992, Alexandria, VA; Abstracts.
  • 18
    • 84913174173 scopus 로고
    • Regarding the use of NaH as the base for the coupling of the β-lactam 2a with the baccatin 3a, see Ref. 4. After the metallation protocol using NaH as the base was worked out in this laboratory, Research Foundation of the State University of New York, Holton presented his new coupling protocol using n-BuLi and lithium amides (LiNRR′) at the 203rd American Chemical Society National Meeting, April 5-10, 1992, San Francisco, CA: Abstracts ORGN 355 (This new protocol was not stated in the abstract).
    • (1992) Invention Disclosure
    • Ojima1    Zucco2
  • 20
    • 84914363663 scopus 로고    scopus 로고
    • β-Lactam 2c was prepared by reacting 1 with TES-Cl in pyridine. β-Lactam 2d was prepared directly from (3R,4S)-3-TBDMS-O-4-phenyl-2-azetidinone which was obtained in 76% yield with 94.5% e.e. through the chiral ester enolate - imine cyclocondensation using (−)-10-dicyclohexylsulfamoyl-D-isobornyl TBDMS-O-acetate, N-TMS-phenylaldimine, and LDA in THF at −90°C. This reaction was reported in our preliminary communication (Ref. 3) with very low chemical yield. Recently, it was found that the low yield was due to the impure N-TMS-phenylaldimine at that time: Georg, G. I. Private communication. The authors thank Professor Gunda I. Georg for informing us of this finding prior to publication.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.