Journal of the American Chemical Society

Total synthesis of (R)-glycerol acetonide and the antiepileptic and hypotensive drug (-)-. gamma.-amino-. beta.-hydroxybutyric acid (GABOB): use of vitamin C as a …

ME Jung, TJ Shaw

Index: Jung, Michael E.; Shaw, Teresa J. Journal of the American Chemical Society, 1980 , vol. 102, # 20 p. 6304 - 6311

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Citation Number: 271

Abstract

Abstract: Ascorbic acid (Vitamin C)(9) is shown to be a useful, inexpensive chiral starting material for natural products synthesis. It is converted in high yield via two synthetic operations into (R)-glycerol acetonide (7), the more inaccessible enantiomer of glycerol acetonide. Since D-(R)-glyceraldehyde acetonide (4) and the corresponding alcohol 1 have been used in many total syntheses of a wide variety of compounds, the ready availability ...

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