Feeding experiments with specifically labelled precursors show that in the biosynthesis of echinuline (8) and neoechinuline (9) from tryptophan (1) the isoprenylation of the benzene ring involves removal of the hydrogen atoms at the positions undergoing alkylation and retention of those at the vicinal positions.
G. Casnati, G. P. Gardini, G. Palla and C. Fuganti, J. Chem. Soc., Perkin Trans. 1, 1974, 2397 DOI: 10.1039/P19740002397
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