Structural Revision of the Hancock Alkaloid (−)-Galipeine | Zendy

Stephen G. Davies | Zendy; Ai M. Fletcher | Zendy; Ian T. T. Houlsby | Zendy; Paul M. Roberts | Zendy; James E. Thomson | Zendy

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Structural Revision of the Hancock Alkaloid (−)-Galipeine

Author(s) -

Stephen G. Davies,

Ai M. Fletcher,

Ian T. T. Houlsby,

Paul M. Roberts,

James E. Thomson

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b01720

Subject(s) - chemistry , alkaloid , stereochemistry , carbon 13 nmr , structural isomer , natural product , absolute configuration , two dimensional nuclear magnetic resonance spectroscopy , organic chemistry

The 1 H and 13 C 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 1 H and 13 C 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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