Identification of a precursor to naturally occurring β-damascenone

CJ Puglisi, GM Elsey, RH Prager, GK Skouroumounis…

Index: Puglisi, Carolyn J; Elsey, Gordon M; Prager, Rolf H; Skouroumounis, George K; Sefton, Mark A Tetrahedron Letters, 2001 , vol. 42, # 39 p. 6937 - 6939

Full Text: HTML

Citation Number: 27

Abstract

9-Hydroxymegastigma-3, 5-dien-7-yne 8a was synthesised and shown to be identical to an intermediate found in the acid-catalysed conversion of 3, 5, 9-trihydroxymegastigma-6, 7- diene 4 to β-damascenone 1, 3-hydroxydamascone 5 and megastigma-5-en-7-yne-3, 9-diol 6. When subjected to acid hydrolysis, 8a produced β-damascenone 1, in high yield. Importantly, the hydrolysate was completely free of 3-hydroxydamascone 5.