Helvetica chimica acta

The Enantioselective Synthesis of β??Amino Acids, their α??hydroxy derivatives, and the N??terminal components of bestatin and microginin

CW Jefford, J McNulty, ZH Lu…

文献索引：Jefford, Charles W.; McNulty, James; Lu, Zhi-Hui; Wang, Jian Bo Helvetica Chimica Acta, 1996 , vol. 79, # 4 p. 1203 - 1216

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被引用次数: 51

摘要

Abstract L-Aspartic acid by tosylation, anhydride formation, and reduction with NaBH 4 was converted into (3S)-3-(tosylamino) butan-4-olide (8; Scheme 1). Tretment of 8 with ethanolic trimethylsilyl iodide gave the N-protected deoxy-iodo-β-homoserine ethyl ester 9. The latter, on successive nucleophilic displacement with lithium dialkyl-cuprates ([RIGHTWARDS ARROW] 10a–e), alkaline hydrolysis ([RIGHTWARDS ARROW] 11a–e), and reductive ...