Acid- and enzyme-catalysed cyclisation reactions of (Z,E)-1(10),4-cyclodecadiene derivatives as model systems for melampolides

✍ Scribed by Dennis P. Piet; Hendra M. Willemen; Theodorus J.M. de Bruin; Maurice C.R. Franssen; Joannes B.P.A. Wijnberg; Aede de Groot

• Book ID: 104207983
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 718 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00723-0

✦ Synopsis

The acid-and enzyme-catalysed cyclisations of a number of (Z,E)-1(10),4-cyclodecadiene derivatives were investigated. In contrast to the regular transannular C-C bond formation as observed for (E,E)-I ( I 0),4-cyclodecadiene systems, these melampolide-like systems cyclised via a number of different reaction pathways in which the oxygen function at C9 plays a crucial role. It was also lbund that these melampolide-like systems preferably react from the anti conformation. This finding is not in agreement with the postulate that melampolides are intermediates in the biosynthesis of trans-fused guaianes. Molecular mechanics and dynamics calculations indicated that the anti conformation is also the conlormation in which these compounds preferably exist.