Total Synthesis of Epothilone B, Epothilone D, andcis- andtrans-9,10-Dehydroepothilone D [J. Am. Chem. Soc.2001,123, 5407−5413].
نویسندگان
چکیده
منابع مشابه
Highly Efficient CYP167A1 (EpoK) dependent Epothilone B Formation and Production of 7-Ketone Epothilone D as a New Epothilone Derivative
Since their discovery in the soil bacterium Sorangium cellulosum, epothilones have emerged as a valuable substance class with promising anti-tumor activity. Because of their benefits in the treatment of cancer and neurodegenerative diseases, epothilones are targets for drug design and pharmaceutical research. The final step of their biosynthesis - a cytochrome P450 mediated epoxidation of epoth...
متن کاملDesign, synthesis and biological evaluation of bridged epothilone D analogues.
Six epothilone D analogues with a bridge between the C4-methyl and the C12-methyl carbons were prepared in an attempt to constrain epothilone D to its proposed tubulin-binding conformation. Ring-closing metathesis (RCM) was employed as the key step to build the C4-C26 bridge. In antiproliferative assays in the human ovarian cancer (A2780) and prostate cancer (PC3) cell lines, and also in tubuli...
متن کاملConformational Properties of Epothilone
The epothilones are macrolide natural products, produced by myxobacterium Sorangium cellulosum (So ce 90), which mimic the biological activity of the anticancer agent Taxol. These interesting compounds have been shown to bind tubulin, induce microtubule polymerization, and stabilize microtubule dynamics. Coupled with its biological activity, epothilone’s relatively simple structure has made it ...
متن کاملMulti-step application of immobilized reagents and scavengers: a total synthesis of epothilone C.
The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.
متن کاملStudies towards the synthesis of epothilone A via organoboranes.
Studies towards the synthesis of epothilone A via organoboranes have been described. A modified procedure for the large-scale preparation of B-gamma,gamma-dimethylallyldiisopinocampheylborane from prenyl alcohol has been developed. This reagent, upon reaction with various aldehydes, provides the corresponding alpha,alpha-dimethylhomoallylic alcohols in high enantioselectivities. The application...
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ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2003
ISSN: 0002-7863,1520-5126
DOI: 10.1021/ja0251221