Issue 20, 2022

Total synthesis and stereochemical assignment of rakicidin F

Abstract

Total synthesis of rakicidin F was accomplished in 20 linear steps (0.68% overall yield), which enabled the configural determination of its six stereogenic centers as 2R, 15R, 16R, 17S, 19S, and 21S. The macrolactonization of the rakicidin linear precursor was investigated and the unsuccessful results might be attributed to the steric hindrance near C16-OH.

Graphical abstract: Total synthesis and stereochemical assignment of rakicidin F

Supplementary files

Article information

Article type
Paper
Submitted
14 Apr 2022
Accepted
29 Apr 2022
First published
30 Apr 2022

Org. Biomol. Chem., 2022,20, 4135-4140

Total synthesis and stereochemical assignment of rakicidin F

F. Han, G. Liu, X. Zhao, S. Du, Y. Ding, Q. Zhang, H. Deng, L. Wang and Y. Chen, Org. Biomol. Chem., 2022, 20, 4135 DOI: 10.1039/D2OB00692H

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