Stereochemistry of the 1,2-migration of the carboxyl group that occurs during the biosynthesis of tropic acid from phenylalanine
(2S,3R)- and (2S,3S)-phenylalanine were fed in separate experiments to Datura innoxia plants.The distribution of isotopes in the resultant labeled hyoscyamine and scopolamine indicates that the biosynthesis of the acid moiety of these ester alkaloids, namely (S)-tropic acid, involves the migration of the carboxyl group of phenylalanine to its prochiral C-3 position with retention of configuration.
Leete, Edward
p. 226 - 228
(2007/10/02)
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