Issue 0, 1979

Alkaloids of Catha edulis. Part 3. Structures of cathedulins K1, K2, K6, and K15; new Macrolide-bridged polyesters of euonyminol

Abstract

It is shown by mass spectral and 1H and 13C n.m.r. methods, together with ethanolysis, that the structure of the polyester alkaloid cathedulin K2 (C40H51NO19) is compiled from euonyminol (1), one evoninic acid residue (cf. 2), five acetic acid residues, and one 2-hydroxyisobutyric acid residue. Some of the ester residues can be positioned on the basis of spectral information. The remainder are assigned as a result of a study of the products formed when cathedulin K2 is treated under controlled conditions with methanolic diethylamine. Four compounds were isolated, C28H37NO13(5), C34H45NO16(6), C36N47NO17(7), and C38H49NO18(8), the structures being assigned spectrally. This leads to the formulation of cathedulin K2 as (4). Using this information, together with further spectral data and information from models, cathedulin K1 (C42H53NO20), K6 (C38H49NO18), and K15 (C36H47NO17) are allocated structures (9), (10), and (11) respectively.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 2976-2981

Alkaloids of Catha edulis. Part 3. Structures of cathedulins K1, K2, K6, and K15; new Macrolide-bridged polyesters of euonyminol

L. Crombie, W. M. L. Crombie, D. A. Whiting and K. Szendrei, J. Chem. Soc., Perkin Trans. 1, 1979, 2976 DOI: 10.1039/P19790002976

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements