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. Author manuscript; available in PMC: 2014 Dec 4.
Published in final edited form as: J Am Chem Soc. 2013 Nov 21;135(48):10.1021/ja409520v. doi: 10.1021/ja409520v

Scheme 1.

Scheme 1

Proposed mechanisms for the stereoselective cyclization of 10 to (S)-1. Deprotonotation of the phenolic hydroxyl facilitates abstraction of the hydride by the FAD cofactor and generation of the intermediate 11. Further nucleophilic attack from the pyrrole-nitrogen yields (S)-1. The presence of molecular oxygen can restore the reduced FADH2 cofactor.