Structure of thalsimine
1. The degradation of thalsimine, dihydrothalsimine, and hernandezine with sodium in liquid ammonia gives rise to derivatives of coclaurine.
2. In thalsimine, besides the splitting of the ether bridges, reduction of the dihydroisoquinoline nucleus takes place.
3. The reduction of thalsimine with zinc in sulfuric acid gives rise to two diastereoisomeric products. Methylation of the latter by Hess's method gives hernandezine and N-methyldihydrothalsimine-B with mp 257–258°, [α]D - 127° (CHCl3).
KeywordsMethyl Iodide Liquid Ammonia Hydrobromic Acid Methiodide Tetrandrine
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