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. Author manuscript; available in PMC: 2019 Apr 1.
Published in final edited form as: Nat Chem Biol. 2018 Mar 12;14(4):345–351. doi: 10.1038/s41589-018-0003-x

Fig. 5. Quantum mechanics analysis.

Fig. 5

a, Cope rearrangement, 6-exo-trig cyclization, and electrophilic aromatic substitution cascade starting from the R enantiomer of substrate 1 in a near-attack conformation, leading to 5 precursor 5P and 6 precursor 6P. The energetics of the Cope rearrangement are computed with the neutral indolenine (pathway N), the N-protonated indolenine (pathway P), and the indolenine forming a hydrogen bond with acetic acid (pathway A). b, Optimized geometry of key intermediate 4P, which undergoes regioselective electrophilic aromatic substitution to form 5 or 6.