title: Total synthesis of ailanthoidol and precursor XH14 by Stille coupling.
abstract: Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.
authors.affiliation: Department of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan.
authors.forename: Shun-Yu
authors.initials: SY
authors.lastname: Lin
authors.forename: Chih-Lung
authors.initials: CL
authors.lastname: Chen
authors.forename: Yean-Jang
authors.initials: YJ
authors.lastname: Lee
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D001572:Benzofurans / Q000032:analysis / Q000138:chemical synthesis*; D002384:Catalysis; D004365:Drugs, Chinese Herbal / Q000737:chemistry; D006139:Guaiacol / Q000031:analogs & derivatives; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D032106:Zanthoxylum / Q000737:chemistry
chemical_list: C476935:5-bromo-2-hydroxy-3-methoxybenzaldehyde; D001547:Benzaldehydes; D001572:Benzofurans; D004365:Drugs, Chinese Herbal; D007202:Indicators and Reagents; C116381:XH-14; C476933:ailanthoidol; D006139:Guaiacol