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O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis.

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The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions… Click to show full abstract

The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.

Keywords: quinic acid; silyl group; migrations quinic; group migrations; synthesis

Journal Title: Organic letters
Year Published: 2021

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