Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata.
[reaction: see text] 13-Hydroxy-14-nordehydrocacalohastine (2) and 13-acetoxy-14-nordehydrocacalohastine (3), two novel modified furanoeremophilane-type sesquiterpenes isolated from Trichilia cuneata, showed inhibitory activities for membrane lipid peroxidation in mitochondria and microsomes. The first, highly convergent total syntheses of new compounds 2 and 3 have also been achieved via a palladium-mediated three-component coupling reaction between 2-iodotoluene (7), 1-penten-4-yn-3-ol (8), and diethyl ethoxymethylenemalonate (9).
Doe
Matsumi
M
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan.
Shibue
Taku
T
Haraguchi
Hiroyuki
H
Morimoto
Yoshiki
Y
D020650:Combinatorial Chemistry Techniques; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D012717:Sesquiterpenes