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.
Synthesis of (+)-Spirolaxine Methyl Ether / R.NANNEI, S.DALLAVALLE, A.BAVA, G.NASINI, L. MERLINI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 71:16(2006 Jul 11), pp. 6277-6280. [10.1021/jo060839i]
Synthesis of (+)-Spirolaxine Methyl Ether
R. NanneiPrimo
;S. DallavalleSecondo
;L. MerliniUltimo
2006
Abstract
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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