SYNTHESIS OF TETRAHYDROLIPSTATIN AND TETRAHYDROESTERASTIN, COMPOUNDS WITH A BETA-LACTONE MOIETY - STEREOSELECTIVE HYDROGENATION OF A BETA-KETO DELTA-LACTONE AND CONVERSION OF THE DELTA-LACTONE INTO A BETA-LACTONE
SYNTHESIS OF TETRAHYDROLIPSTATIN AND TETRAHYDROESTERASTIN, COMPOUNDS WITH A BETA-LACTONE MOIETY - STEREOSELECTIVE HYDROGENATION OF A BETA-KETO DELTA-LACTONE AND CONVERSION OF THE DELTA-LACTONE INTO A BETA-LACTONE
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DOI：
10.1021/jo00241a018
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发表时间：
1988-03-18
影响因子：
3.6
通讯作者：
SCHNEIDER, F
中科院分区：
文献类型：
--
作者：
BARBIER, P;SCHNEIDER, F
Stereoselective syntheses of tetrahydrolipstatin (1) and tetrahydroesterastin (2) are described. The key intermediate .beta.-keto .delta.-lactone 7 is hydrogenated stereoselectively to yield hydroxy .delta.-lactone 9, which is transformed into hydroxyl .beta.-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 .beta.-lactone 18. Reaction of the lattter with the mixed anhydride of (S)-N-Z-asparagine, hydrogenation, and acetylation give tetrahydroesterastin (2).
