Application of the DP4 Probability Method to Flexible Cyclic Peptides with Multiple Independent Stereocenters: The True Structure of Cyclocinamide A

2018: Organic Letters

https://doi.org/10.1021/acs.orglett.8b01756

Jason K. Cooper, Kelin Li, Jeffrey Aube, David A. Coppage, Joseph P. Konopelski*

A DP4 protocol has been successfully utilized to establish the true structure of the natural product cyclocinamide A, a flexible cyclic peptide with four isolated stereocenters. Benchmarking the necessary level of theory required to successfully predict the NMR spectra of three previously synthesized isomers of cyclocinamide A led to the prediction of the natural stereochemistry as 4S, 7R, 11R, 14S, which has been confirmed by total synthesis.

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