9.93 Monensin is a potent antibiotic compound isolated from Streptomyces cinnamonensis. The following reaction was employed...

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9.93 Monensin is a potent antibiotic compound isolated from Streptomyces cinnamonensis. The following reaction was employed dur- ing W. C. Still's synthesis of monensin (J. Am. Chem. Soc. 1980, 102, 2118-2120). Sodium bicarbonate (NaHCO3) functions as a mild base to deprotonate the carboxylic acid group. The transformation is said to be diastereoselective, because only one diastereomeric product (55,65) is obtained. The other expected diastereomer (5R,6R) is not observed. 6 H-O 3 NaHCO3 12 1 (a) Draw a mechanism for this transformation. H H O 2 9.93 Monensin is a potent antibiotic compound isolated from Streptomyces cinnamonensis. The following reaction was employed dur- ing W. C. Still's synthesis of monensin (J. Am. Chem. Soc. 1980, 102, 2118-2120). Sodium bicarbonate (NaHCO3) functions as a mild base to deprotonate the carboxylic acid group. The transformation is said to be diastereoselective, because only one diastereomeric product (55,65) is obtained. The other expected diastereomer (5R,6R) is not observed. 6 H-O 3 NaHCO3 12 1 (a) Draw a mechanism for this transformation. H H O 2

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