Total synthesis of ailanthoidol and precursor XH14 by Stille coupling.
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.
Lin
Shun-Yu
SY
Department of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan.
Chen
Chih-Lung
CL
Lee
Yean-Jang
YJ
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
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