Kurasoins A and B, new protein farnesyltransferase inhibitors produced by Paecilomyces sp. FO-3684. II. Structure elucidation and total synthesis.
نویسندگان
چکیده
The structures of new protein farnesyltransferase inhibitors, kurasoins A and B, were elucidated by NMR study. Kurasoins A and B are acyloin compounds having in common a 3-hydroxy-1-phenyl-2-butanone moiety, to which p-hydroxyphenyl and 3-indolyl moieties respectively, are connected at C-4. The structures were confirmed by total synthesis.
منابع مشابه
Kurasoins A and B, new protein farnesyltransferase inhibitors produced by Paecilomyces sp. FO-3684. I. Producing strain, fermentation, isolation, and biological activities.
sample collected at Kurashiki City, OkayamaPrefecture, Japan. From the characteristics described below, the fungus was identified as a strain of Paecilomyces sp. For the identification of the fungus, potato-dextrose agar (PDA), yeast extract-soluble starch agar (YpSs), and corn meal agar (CMA) were used. Colonies on CMAgrew rather restrictedly, attaining a diameter of 20~25mmand was colored in ...
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(70% of theory) and >90% ee, as determined by NMR analysis of the derived ( + )-MTPA ester.5) Protection of (-)-6 by TBSC1 and imidazole afforded (-)-7f in 71% yield. Stereospecific alkylation of epoxide (-)-7 with phenylmagnesium bromide in the presence of Cul afforded the (-)-8f in 75% yield. Moffat oxidation (DCC, TFA, pyridine, DMSO, benzene) of (-)-8 furnished (-)-9t (88%). Finally, remova...
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ورودعنوان ژورنال:
- The Journal of antibiotics
دوره 49 9 شماره
صفحات -
تاریخ انتشار 1996