2008 Eighth Annual Beckman Scholars Symposium
Thursday Poster Session - July 27, 2006

Scott Bresler
Department of Chemistry
Miami University
Synthetic Studies of Several Bioactive, Naturally Occurring Polyacetylenes
Various polyacetylenic compounds, in addition to possessing fascinating chemical properties, have also been shown to be active in a wide range of biological systems. Here, the synthesis of 1,3R,8R-trihydroxydec-9-en-4,6-yne, a Polyacetylenic 12-lipoxygenase inhibitor from Artemisia monosperma, as well as an outline for the synthesis of its glucoside, are presented. Furthermore, an attempt of the total synthesis of trideca-3,5,7,9,11-pentayne-1,2-diol, a naturally occurring pentayne from Microglossa pyrifolia is detailed. Experimental procedures and spectroscopic data were recorded for each novel compound synthesized. Although the true configuration of naturally occurring 1,3R,8R-trihydroxydec-9-en-4,6-yne was not established, all possible stereoisomers were synthesized and their optical activities were measured.