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Complete assignment of the 1H and 13C NMR spectra of the Coccinellidae-defensive alkaloids myrrhine, precoccinelline and hippodamine, their N -oxides and the corresponding hydrochlorides

✍ Scribed by B. Lebrun; J. C. Braekman; D. Daloze

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 85 KB
Volume: 37
Category: Article
ISSN: 0749-1581
DOI: 10.1002/(sici)1097-458x(199901)37:1<60::aid-mrc417>3.0.co;2-g

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✦ Synopsis

The 1H and 13C NMR spectra of the 2-methylperhydro-9b-azaphenalene alkaloids characteristic of coccinellid beetles, myrrhine, precoccinelline, hippodamine, their N-oxides and the corresponding hydrochlorides were completely assigned for the Ðrst time by a one-and two-dimensional homo-and heteronuclear study (1H, 13C, 1HÈ1H COSY, HMQC, HMBC) at 600 and 150.87 MHz. The inÑuence of the ring junction stereochemistry and of the N-oxide function on the proton and carbon chemical shifts in this series of compounds is discussed. Protonation shifts are also considered 1999 John Wiley & Sons, Ltd.

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