1186138-10-2Relevant academic research and scientific papers
Structural revision of the hancock alkaloid (-)-galipeine
Davies, Stephen G.,Fletcher, Ai M.,Houlsby, Ian T.T.,Roberts, Paul M.,Thomson, James E.
, p. 10673 - 10679 (2017)
The 1H and 13C NMR data of synthetic samples of (S)-N1-methyl-2- [2′-(3″-hydroxy-4″-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline, the originally proposed structure of the Hancock alkaloid (-)-galipeine, do not match those of the natural product. Herein, the preparation of the regioisomer (S)-N1-methyl-2-[2′- (3″-methoxy-4″-hydroxyphenyl)ethyl]-1,2,3,4-tetrahydroquinoline is reported, the 1H and 13C NMR data of which are in excellent agreement with those of (-)-galipeine. Comparison of specific rotation data enables assignment of the absolute (S)- configuration of the alkaloid, and together, these data engender the structural revision of (-)-galipeine to (S)-N1-methyl-2-[2′-(3″-methoxy-4″-hydroxyphenyl)ethyl]- 1,2,3,4-tetrahydroquinoline.
