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Volumn , Issue 9, 2001, Pages 1701-1714

Methodology based on chiral silanes in the synthesis of polypropionate-derived natural products - Total synthesis of epothilone A

Author keywords

Antitumor natural products; Asymmetric synthesis; Chiral silane reagent; Epothilone; Lipase resolution

Indexed keywords

EPOTHILONE A; EPOTHILONE B; NATURAL PRODUCT; PROPIONIC ACID; SILANE DERIVATIVE; TAXOL; TRIACYLGLYCEROL LIPASE;

EID: 0035034609     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:9<1701::AID-EJOC1701>3.0.CO;2-%23     Document Type: Article
Times cited : (45)

References (47)
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    • note
    • Pseudomonas AK lipase was purchased from Amano International Enzyme Co. for S 100/100 g.
  • 28
    • 0010771837 scopus 로고
    • For chelation-controlled addition to carbonyl groups see: M. Reetz, Angew. Chem. Int. Ed. Engl. 1984, 23, 556-569.
    • (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 556-569
    • Reetz, M.1
  • 32
    • 0002206257 scopus 로고    scopus 로고
    • For a review on the use of enzymes for the preparation of natural products and analogs, see: S. M. Roberts, N. M. Williamson, Curr. Org. Chem. 1997, 1, 1-20.
    • (1997) Curr. Org. Chem. , vol.1 , pp. 1-20
    • Roberts, S.M.1    Williamson, N.M.2
  • 35
    • 85050296727 scopus 로고
    • 1H NMR spectroscopic analysis of crude mandelate ester derived from the chiral alcohol and (R)-O-acetylmandelic acid.
    • (1988) Top. Stereochem. , vol.18 , pp. 249-330
    • Kagan, H.B.1    Fiaud, J.C.2
  • 37
    • 84863240389 scopus 로고
    • For literature precedents of lipase resolution of divinyl carbinols, see: K. Burgess, L. D. Jennings, J. Am. Chem. Soc. 1990, 112, 7434-7436.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7434-7436
    • Burgess, K.1    Jennings, L.D.2
  • 40
    • 85197325274 scopus 로고    scopus 로고
    • note
    • [10b]
  • 42
    • 85197321836 scopus 로고    scopus 로고
    • note
    • Several attempts to couple the C5 ketone (below) with vinyl iodide 5 under Suzuki conditions afforded the cis-olefin, but in much lower yields (33-40%). (Chemical Equation Presented)
  • 47
    • 85197334222 scopus 로고    scopus 로고
    • note
    • [25c] Professor Danishefsky has informed us that the epoxidation can be carried with useful levels of selectivity providing the DMDO solution be kept cold during the addition to the solution of olefin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.