Identification of a precursor to naturally occurring beta-damascenone

Authors
Puglisi, CJ Elsey, GM Prager, RH Skouroumounis, GK Sefton, MA
Citation
Cj. Puglisi et al., Identification of a precursor to naturally occurring beta-damascenone, TETRAHEDR L, 42(39), 2001, pp. 6937-6939
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
39
Year of publication
2001
Pages
6937 - 6939
Database
ISI
SICI code
0040-4039(20010924)42:39<6937:IOAPTN>2.0.ZU;2-U
Abstract
9-Hydroxymegastigma-3,5-dien-7-yne 8a was synthesised and shown to be ident ical to an intermediate found in the acid-catalysed conversion of 3,5,9-tri hydroxymegastigma-6,7-diene 4 to beta -damascenone 1, 3-hydroxydamascone 5 and megastigma-5-en-7-yne-3,9-diol 6. When subjected to acid hydrolysis, 8a produced beta -damascenone 1, in high yield. Importantly, the hydrolysate was completely free of 3-hydroxydamascone 5. (C) 2001 Elsevier Science Ltd. All rights reserved.