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High resolution proton nmr and carbon 13 nmr spectra of saturated pyrrolizidine mono ester alkaloids



High resolution proton nmr and carbon 13 nmr spectra of saturated pyrrolizidine mono ester alkaloids



Journal of Natural Products (Lloydia) 45(3): 328-336



1H NMR spectra of saturated pyrrolizidine monoester alkaloids and the aminoalcohols trachelanthamidine, isoretronecanol, supinidine and curassanecine [from Heliotropium curassavicum] were determined at 270 MHz in CDCl3 and C6D6. Chemical shifts and coupling constants are tabulated. Evidence is presented that viridiflorates and trachelanthates can be differentiated by means of chemical shifts of the magnetically non-equivalent isopropyl methyl groups in C6D6 and chemical shifts and patterns of the H-4' and H-9 signals. 13C-NMR spectra of these substances measured at 67.89 MHz are also reported. Chemical shift trends are presented and another method for distinguishing viridifloric and trachelanthic esters on the basis of the chemical shifts of the methyl C is discussed.

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