Issue 20, 2022
From the journal:

Organic & Biomolecular Chemistry

Total synthesis and stereochemical assignment of rakicidin F†

Fangzhi Han,‡a   Guangju Liu,‡a   Xiuhe Zhao,a   Shunshun Du,a   Yahui Ding,b   Quan Zhang,a   Huiting Deng,c   Liang Wang ORCID logo *b  and  Yue Chen ORCID logo b  

* Corresponding authors

a The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin, People's Republic of China

b College of Chemistry, Nankai University, Tianjin, People's Republic of China
E-mail: lwang@nankai.edu.cn

c Nankai University, Tianjin Third Central Hospital affiliated to Nankai University, Tianjin Key Laboratory of Extracorporeal Life Support for Critical Diseases, Institute of Hepatobiliary Disease, Tianjin, People's Republic of China

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

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Article information

DOI
https://doi.org/10.1039/D2OB00692H
Article type
Paper
Submitted
14 Apr 2022
Accepted
29 Apr 2022
First published
30 Apr 2022

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

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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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