Oct 2013 - Article in Acta Cryst. C Published

Keith Andrews' paper on a ring-closing metathesis approach to decalins is published in Acta Cryst. Sect. C

K.G. Andrews, C.S. Frampton, A.C. Spivey, 'Structural Assignment of a bis-Cyclopentenyl-beta-cyanohydrin Formed via Alkene Metathesis from either a Triene or a Tetraene Precursor', Acta Cryst. Sect. C.  [Special Issue on "Pharmaceuticals, Drug Discovery and Natural Products" Edited  by C.S. Frampton], 2013, 69, 1207-1211, DOI: 10.1107/S010827011302492X

The identity of the major product of Ru-catalysed alkene metathesis of two polyene substrates has been determined using Density Functional Theory (DFT) NMR prediction, a ¹H-¹H TOCSY NMR experiment and ultimately by single crystal X-ray crystallography. The substrates were designed as ones that would potentially allow expedient access to the trans-decalin skeleton of the natural product (-)-euonyminol but the product was found to be a bis-cyclopentenyl-beta-cyanohydrin rather than the trans-2,3,6,7-dehydrodecalin-beta-cyanohydrin.