The Absolute Structure of Latifoline

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.