Bioinspired Total Synthesis of Complex Nucleoside Antibiotics A201A,A201D and A201E |
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| Authors: | Jiaxiang Wang Jiahui Gao Tianyun Guo Prof Dr Xing Huo Prof Dr Wenhua Zhang Prof Dr Jian Liu Prof Dr Xiaolei Wang |
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| Institution: | 1. State Key Laboratory of Applied Organic Chemistry, Department of Chemistry and School of Pharmacy, Lanzhou University, Lanzhou, 730000 P. R. China;2. School of Life Sciences, Lanzhou University, Lanzhou, 730000 P. R. China |
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| Abstract: | Herein, bioinspired total syntheses of A201A, A201D, and A201E based on a previously reported biosynthetic pathway are presented. The challenging 1,2-cis-furanoside, a core structure of the A201 family, was obtained by remote 2-quinolinecarbonyl-assisted glycosylation. We accomplished the total synthesis of A201A and A201E based on the critical 1,2-cis-furanoside moiety through late-stage glycosylation without any interference from basic dimethyl adenosine. We also confirmed the absolute configuration of A201E by total synthesis. This modular synthesis strategy enables efficient preparation of A201 family antibiotics, allowing the study of their structure–activity relationships and mode of action. This study satisfies the increasing demand for developing novel antibiotics inspired by the A201 family. |
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| Keywords: | Carbohydrates Hydrogen-Bond-Assisted Glycosylation Natural Products Nucleoside Antibiotics Total Synthesis |
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