M. Ansarin et Jg. Woolley, THE BIOSYNTHESIS OF TROPIC ACID .5. THE REARRANGEMENT OF PHENYLLACTATE IN THE BIOSYNTHESIS OF TROPIC ACID, Phytochemistry, 35(4), 1994, pp. 935-939
Phenyl [1,3-C-13(2)] lactic acid was synthesized and fed to Datura str
amonium via the wick method and via the roots. Hyoscine (scopolamine)
and hyoscyamine were isolated, and examination of their C-13 NMR spect
ra showed spin-spin coupling from the newly formed contiguous centres,
indicating that tropic acid is formed by an intramolecular rearrangem
ent of phenyllactate.