Journal of Organic Chemistry 2003-04-04

Total synthesis of ailanthoidol and precursor XH14 by Stille coupling.

Shun-Yu Lin, Chih-Lung Chen, Yean-Jang Lee

Index: J. Org. Chem. 68(7) , 2968-71, (2003)

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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.