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Structural Revision of the Hancock Alkaloid (−)-Galipeine

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posted on 15.08.2017, 00:00 authored by Stephen G. Davies, Ai M. Fletcher, Ian T. T. Houlsby, Paul M. Roberts, James E. Thomson
The 1H and 13C NMR data of synthetic samples of (S)-N(1)-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)-N(1)-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)-N(1)-methyl-2-[2′-(3″-methoxy-4″-hydroxyphenyl)­ethyl]-1,2,3,4-tetrahydroquinoline.

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