In our efforts to develop new rifamycin anti-biotics we needed to improve the reported procedure to produce C17-C18 epoxide derivatives.   The reported peracid procedure gave a complex mixture of products that were difficult to separate and gave low yields of the desired compound.  In an attempt to improve the synthetic yield, we used a vanadium metal catalyzed epoxidation method that relied on the directing effect of an adjacent alcohol group that directed the epoxidation to one face of the rifamycin scaffold.   We were encouraged by the appearance of a single new product with the correct molecular weight.  Unfortunately, the <sup>1</sup>H NMR spectrum of this new single product was not consistent with any of the reported rifamycin epoxide spectra. We believe that the new product is a previously unknown rifamycin derivative in which the adjacent amide has facilitated a rearrangement reaction of the epoxide to a new 2-aminofuran derivative.  We will show data that demonstrates the new furan derivative can be formed from one of the previously reported rifamycin epoxides in the presence of the vanadium epoxidation catalyst.  We will also show that the other rifamycin epoxide derivatives previously reported are unchanged in the presence of a vanadium catalyst for up to 24 hours.<br/>

Novel arrangement of a 3-(oxiran-2-yl)prop-2-enamide to a 2-amino furan rifamycin derivative

2019 Spring National Meeting

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