4.7 Article

Synthesis of (+)-spirolaxine methyl ether

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 16, Pages 6277-6280

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo060839i

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A short and efficient synthesis of (+)-spirolaxine methyl ether, a metabolite of the fungus Sporotrichum laxum with inhibitory activity against Helicobacter pylori, is described. The synthesis has been carried out by a Prins cyclization, to obtain the [ 6,5]-spiroketal system, and a Wadsworth-Emmons condensation, applied for the installation of the polymethylene chain on the phthalide moiety.

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