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Scientific article
English

The Enantioselective Synthesis of β-Amino Acids, Their α-Hydroxy Derivatives, and the N-Terminal Components of Bestatin and Microginin

Published inHelvetica Chimica Acta, vol. 79, no. 4, p. 1203-1216
Publication date1996
Abstract

L‐Aspartic acid by tosylation, anhydride formation, and reduction with NaBH₄ 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 ( → 10a–e), alkaline hydrolysis ( → 11a–e), and reductive removal of the tosyl group, produced the corresponding 4‐substituted (3R)‐3‐aminobutanoic acids 12a–e (ee > 99%). Electrophilic hydroxylation of 8 ( → 19; Scheme 3), subsequent iodo‐esterification ( → 21; Scheme 4), and nucleophilic alkylation and phenylation afforded, after saponification and deprotection, a series of 4‐substituted (2S, 3R)‐3‐amino‐2‐hydroxybutanoic acids 24 including the N‐terminal acids 24e ( =3) and 24f ( =4) of bestatin and microginin (de > 95%), respectively.

Citation (ISO format)
JEFFORD, Charles Edward et al. The Enantioselective Synthesis of β-Amino Acids, Their α-Hydroxy Derivatives, and the <i>N</i>-Terminal Components of Bestatin and Microginin. In: Helvetica Chimica Acta, 1996, vol. 79, n° 4, p. 1203–1216. doi: 10.1002/hlca.19960790426
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ISSN of the journal0018-019X
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