Post-tyrosine intermediates in the biosynthesis of mesembrine alkaloids and stereochemistry of protonation at C-7 in the formation of the octahydroindole skeleton
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 3,p. 82-83
- https://doi.org/10.1039/c39760000082
Abstract
The biosynthesis of (–)-mesembrenol is shown to involve the sequential intermediates, tyrosine → tyramine →N-methyltyramine, which when labelled at their symmetry equivalent 3,5-positions lead to a 50% loss of tritium leaving the remaining tritium equally distributed between the H-5 and H-7α positions; this result indicates that a stereospecific protonation at C-7 occurs from the β-face during the late stages of the biosynthesis.This publication has 0 references indexed in Scilit: