Convergent Total Synthesis of Yaku'amide A,Angewandte Chemie International Edition

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Convergent Total Synthesis of Yaku'amide A
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-12-17 , DOI: 10.1002/anie.202014238
Yu Cai ₁ , Zhiwei Ma ₁ , Jintao Jiang ₁ , Concordia C L Lo ₁ , Shi Luo ₁ , Ankur Jalan ₁ , Joseph M Cardon ₁ , Alexander Ramos ₁ , Diego A Moyá ₁ , Daniel Joaquin ₁ , Steven L Castle ₁

Affiliation

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.

中文翻译：

Yaku'amide A的聚合全合成

报道了抗癌肽天然产物yaku'amide A的全合成。它的β-叔羟基氨基酸是通过区域选择性氨基羟基化反应制备的，涉及手性甲磺氧基氨基甲酸酯试剂。E-和Z -ΔIle残基的立体特异性构建是通过具有抗脱水、叠氮化物还原和O→N酰基转移的单锅反应完成的。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种高度收敛和有效的合成路线。

更新日期：2021-02-22

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