Phenyllactic acid rearrangement

Ansarin, M. and Woolley, J.G. (1994) The rearrangement of phenyllactic acid in the bios)mthesis of tropic acid. Phytochemistry, 35, 935-9. 

Decarboxylation is followed by oxidative cycliza-tion to tropinone, followed by stereospecific reduction to the a-Hydroxy group, which is esterified to hyoscya-mine. The esterifying ester, tropic acid, is an intramo-lecularly rearranged phenyllactic acid (derived from phenylalanine). Further elaboration of hyoscyamine yields scopolamine (Fig. 23). The enzymes for this transformation are known. 

Fig. (4). Possible rearrangement of phenyllactic acid or alanine derivatives...

Chesters, N.C.J.E., O Hagan, D. and Robins, R.J. (1994) The biosynthesis of tropic acid in plants evidence for the direct rearrangement of phenyllactate to tropate. /. Chem. Soc. Perkin Trans., 1,1159-62. 

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