WYE-120318, a ring contraction product of methylnaltrexone, and structure revision of coniothyrione (pages 829–833)
Fangming Kong, Tianmin Zhu, Weitao Pan, Russ Tsao, Thomas G. Pagano, Bao Nguyen and Brian Marquez
Article first published online: 8 NOV 2012 | DOI: 10.1002/mrc.3892
A contracted ring degradation product, WYE-120318 (compound 2), was discovered during the development phase for methylnaltrexone bromide (compound 1) drug substance. The compound was isolated, and its structure was determined by spectroscopic data analyses. Remisporine A (compound 3) is envisioned as a naturally occurring ring contraction compound that autocatalytically dimerizes to dimer 4. Coniothyione (compound 5) can be considered as the first example of a stable natural product bearing the remisporine A skeleton. However, the regiochemistry of the chlorosubstituent needs to be revised to compound 6.