Tetrahedron: Asymmetry

Chemo-enzymatic synthesis of both enantiomers of rugulactone

G Reddipalli, M Venkataiah, NW Fadnavis

Index: Reddipalli, Gowrisankar; Venkataiah, Mallam; Fadnavis, Nitin W. Tetrahedron Asymmetry, 2010 , vol. 21, # 3 p. 320 - 324

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Citation Number: 16

Abstract

The synthesis of both the (R)-and (S)-enantiomers of the natural product rugulactone has been achieved. Candida rugosa lipase hydrolyzes the butyrate ester of the protected 3- hydroxy homoallylic alcohol with very high enantioselectivity (E= 244) and provides the key intermediates with high enantiomeric purity (ee 98–99%) and excellent yields.