Tetrahedron: Asymmetry

Synthetic routes to L-carnitine and L-gamma-amino-beta-hydroxybutyric acid from (S)-3-hydroxybutyrolactone by functional group priority switching

G Wang, RI Hollingsworth

Index: Wang, Guijun; Hollingsworth, Rawle I. Tetrahedron Asymmetry, 1999 , vol. 10, # 10 p. 1895 - 1901

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Citation Number: 47

Abstract

(R)-3-Hydroxy-4-trimethylaminobutyric acid (l-carnitine) and (R)-4-amino-3-hydroxybutyric acid (GABOB) are two compounds with a very high level of medical significance. They can be prepared from (R)-3-hydroxy-γ-butyrolactone which is not readily available in significant quantities. The corresponding (S)-lactone is available in large quantities but attempts at inverting the stereochemistry of the hydroxyl group lead to elimination to give the furanone ...

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