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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Article Synopsis
- Several naturally occurring antibiotics contain phthalides and have shown effectiveness against Helicobacter pylori, but the specific stereochemistry related to this activity remains unconfirmed.
- A 1:1 mixture of specific spiroacetals with (3R)-stereochemistry demonstrated significantly higher anti-H. pylori activity compared to those with (3S)-stereochemistry.
- Additionally, the unnatural diastereomer of spirolaxine methyl ether was more effective than its natural counterpart, suggesting potential avenues for drug development.
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