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Concise enantiospecific syntheses of α-hydroxy-β-amino acids and indolizidines of natural origin

Published inPure and Applied Chemistry, vol. 66, no. 10/11, p. 2075-2078
Publication date1994
Abstract

A new procedure has been developed for synthesizing enantiomerically pure β-amino acids, α-hydroxy-β-amino acids and certain alkaloids from aspartic acid. By protection, anhydride formation and regioselective reduction, L-aspartic 10 is converted to the N-tosylamino lactone 12. Hydroxylation of 12 by an oxaziridine gives the trans-2-hydroxy-3-N-tosylamino derivative 20. Opening of 12 and 20 by trimethylsilyl iodide and ethanol affords the iodo-homoserine esters 13 and 21 respectively. Submission of 13 and 21 to Gilman reagents followed by saponification and deprotection gives 4-substituted 3-amino and 3-amino-2-hydroxybutyric acids (15 and 23), exemplified by the syntheses of cyclohexylnorstatine (25), and the components of bestatin (23, R=Ph) and microginin (14). Certain β-amino acids are transformed into solenopsin A (33) and indolizidine 209D (41).

Funding
  • Swiss National Science Foundation - 20-32'166.91
Citation (ISO format)
JEFFORD, Charles, LU, Zhi-Hui, WANG, Jian Bo. Concise enantiospecific syntheses of α-hydroxy-β-amino acids and indolizidines of natural origin. In: Pure and Applied Chemistry, 1994, vol. 66, n° 10/11, p. 2075–2078. doi: 10.1351/pac199466102075
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ISSN of the journal0033-4545
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