Total synthesis and stereochemical assignment of rakicidin F

Fangzhi Han; Guangju Liu; Xiuhe Zhao; Shunshun Du; Yahui Ding; Quan Zhang; Huiting Deng; Liang Wang; Yue Chen

doi:10.1039/d2ob00692h

Total synthesis and stereochemical assignment of rakicidin F

Org Biomol Chem. 2022 May 26;20(20):4135-4140. doi: 10.1039/d2ob00692h.

Authors

Fangzhi Han¹, Guangju Liu¹, Xiuhe Zhao¹, Shunshun Du¹, Yahui Ding², Quan Zhang¹, Huiting Deng³, Liang Wang², Yue Chen²

Affiliations

¹ The State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin, 300350, People's Republic of China.
² College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China. lwang@nankai.edu.cn.
³ 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, 300170, People's Republic of China.

PMID: 35510627
DOI: 10.1039/d2ob00692h

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Structure*
Stereoisomerism