Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, 84602, USA.
Angew Chem Int Ed Engl. 2021 Mar 1;60(10):5162-5167. doi: 10.1002/anie.202014238. Epub 2021 Jan 21.
Total synthesis of the anticancer peptide natural product yaku'amide A is reported. Its β-tert-hydroxy amino acids were prepared by regioselective aminohydroxylation involving a chiral mesyloxycarbamate reagent. Stereospecific construction of the E- and Z-ΔIle 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.
本文报道了抗癌肽天然产物 yaku'amide A 的全合成。其 β-叔羟基氨基酸通过涉及手性甲氧基羰基试剂的区域选择性氨羟化反应来制备。通过一锅反应实现了 E-和 Z-ΔIle 残基的立体特异性构建，该反应具有反脱水、叠氮还原和 O→N 酰基转移等反应。在此过程中，烯烃异构化可忽略不计。这些方法为天然产物提供了一条高度收敛且高效的合成路线。
