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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Absolute Structure of Latifoline

CCJ Culvenor and MF Mackay

Australian Journal of Chemistry 45(2) 451 - 456
Published: 1992

Abstract

The absolute structure of latifoline, a pyrrolizidine diester alkaloid of retronecine and latifolic and angelic acids, has been defined by single-crystal X-ray crystallographic analysis of the hydrobromide salt hydrate. Orthorhombic crystals of C20H27NO7.HBr.H2O belong to the space group P 2′2′2′ with a 7.279(1), b 17.898(3), c 17.922(2) Å and V 2334-9(8) Å 3 . The structure has been refined to an R index of 0.054 for 1725 observed terms. The absolute configuration has been assigned by comparison with that of retronecine and also determined independently by X-ray examination of selected Bijvoet pairs. Our results have shown that the absolute structure of latifolic acid is 13S,14R,19S (2R,3S,4S in latifolic acid numbering), and not the stereoisomer reported recently by Roitman and Wong.

https://doi.org/10.1071/CH9920451

© CSIRO 1992

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