The synthesis of functionalized nitriles via microwave-promoted radical fragmentations of cyclic O-phenyl oxime ethers is reported. A variety of radical traps can be employed, permitting the generation of diverse adducts via C-O, C-C, C-N, or C-X bond formation. Other salient features include a simple and practical protocol, very short reaction times, and the avoidance of metal catalysts and toxic cyanide reagents. The utility of this method is demonstrated by the ring-distortion of a steroid-derived substrate.
Total synthesis of the anticancer peptide natural product yakuamide A is reported. Its b-tert-hydroxy amino acids were prepared by regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecific construction of the E-and Z-DIle residues was accomplished through a one-pot reaction featuring anti dehydration, azide reduction, and O!N acyl transfer. Alkene isomerization was negligible during this process. These methods enabled a highly convergent and efficient synthetic route to the natural product.
Total synthesis of the anticancer peptide natural product yakuamide A is reported. Its b-tert-hydroxy amino acids were prepared by regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecific construction of the E-and Z-DIle residues was accomplished through a one-pot reaction featuring anti dehydration, azide reduction, and O!N acyl transfer. Alkene isomerization was negligible during this process. These methods enabled a highly convergent and efficient synthetic route to the natural product.
Two full-length analogs of the anticancer peptide yaku’amide A (1a) and four partial structures have been synthesized. These analogs were identified by computational studies in which the three E- and...
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