Studies directed toward the synthesis of ulapualide A. Asymmetric synthesis of the C8-C25 tris-oxazole fragment

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6496-6497

  Panek, James S ^a   Beresis, Richard T ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ULAPUALIDE A; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029840044     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960532r     Document Type: Article

References (20)

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2. The numbering system employed is that used in the isolation publication of ulapualide A; see Roesener, J. A; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846-847.
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15. 13C NMR, IR, MS, and HRMS) were obtained for all new compounds.
16. 3 (5.0 equiv), in refluxing THF for 15 h followed by a second charge with ethyl bromopyruvate and an additional 8 h reflux period. Following filtration of solids and concentration under reduced pressure, the crude hydroxvoxazole was quantitatively converted to the oxazole through treatment with TFAA in THF at 0 °C.
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