112764-03-1Relevant articles and documents
Synthesis of Tetrahydrolipstatin and Tetrahydroesterastin, Compounds with a β-Lactone Moiety. Stereoselective Hydrogenation of a β-Keto δ-Lactone and Convertion of the δ-Lactone into a β-Lactone
Barbier, Pierre,Schneider, Fernand
, p. 1218 - 1221 (2007/10/02)
Stereoselective syntheses of tetrahydrolipstatin (1) and tetrahydroesterastin (2) are described.The key intermediate β-ketoδ-lactone 7 is hydrogenated stereoselectively to yield hydroxy δ-lactone 9, which is transformed into hydroxy β-lactone 10.Esterification of 10 with (S)-N-formylleucine under Mitsunobu's conditions yields tetrahydrolipstatin (1).Esterification of 10 with (S)-N-acetylasparagine under the same conditions yields 17 (mixture of two diastereomers), which gives by saponification hydroxy β-lactone 18.Reaction of the latter with the mixed anhydride of (S)-N-Z-asparagine, hydrogenation, and acetylation give tetrahydroesterastin (2).
