Total Synthesis and Determination of the Absolute Configuration of Rakicidin C

Fangzhi Han; Guangju Liu; Chaofan Jin; Jinghan Wang; Jianwei Liu; Liang Wang; Yue Chen

doi:10.1021/acs.orglett.1c02476

Total Synthesis and Determination of the Absolute Configuration of Rakicidin C

Org Lett. 2021 Sep 17;23(18):7069-7073. doi: 10.1021/acs.orglett.1c02476. Epub 2021 Aug 30.

Authors

Fangzhi Han¹, Guangju Liu¹, Chaofan Jin¹, Jinghan Wang¹, Jianwei Liu¹, Liang Wang^{1

2}, Yue Chen^{1

2}

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.

PMID: 34459614
DOI: 10.1021/acs.orglett.1c02476

Abstract

The absolute configuration of rakicidin C was predicted by comparison of optical rotation data and absolute configuration of APD-cyclic depsipeptides and further determined by total synthesis. The absolute configuration of five chiral centers was determined as 2R, 15R, 16R, 17S, and 19S. Our efficient route involves 19 longest linear steps with an overall yield of 1.49%.

Publication types

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