Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata

Matsumi Doe; Taku Shibue; Hiroyuki Haraguchi; Yoshiki Morimoto

doi:10.1021/ol050346k

Structures, biological activities, and total syntheses of 13-hydroxy- and 13-acetoxy-14-nordehydrocacalohastine, novel modified furanoeremophilane-type sesquiterpenes from Trichilia cuneata

Org Lett. 2005 Apr 28;7(9):1765-8. doi: 10.1021/ol050346k.

Authors

Matsumi Doe¹, Taku Shibue, Hiroyuki Haraguchi, Yoshiki Morimoto

Affiliation

¹ Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan.

PMID: 15844901
DOI: 10.1021/ol050346k

Abstract

[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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Combinatorial Chemistry Techniques
Meliaceae / chemistry*
Molecular Structure
Plants, Medicinal / chemistry*
Sesquiterpenes* / chemical synthesis
Sesquiterpenes* / chemistry
Sesquiterpenes* / pharmacology

Substances

Sesquiterpenes