ENANTIOSELECTIVE SYNTHESIS OF HYDROXY ALPHA-AMINO-ACIDS - (-)-ERYTHRO-GAMMA-HYDROXYNORVALINES AND (-)-THREO-GAMMA-HYDROXYNORVALINES

被引:38
作者
ARIZA, J [1 ]
FONT, J [1 ]
ORTUNO, RM [1 ]
机构
[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,UNITAT QUIM ORGAN,E-08193 BARCELONA,SPAIN
关键词
D O I
10.1016/S0040-4020(01)89761-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The amino acids (-)-erythro- and (-)-threo-γ-hydroxynorvaline have been synthesized from D-ribonolactone, 6, as single chiral precursor. Moreover, β-hydrox-αazido- γ-valerolactones 12a and 12b have been also prepared from 6 in two different alternative ways. These compounds afford β,γ-dihydroxy-α -amino acids 18a and 18b with Darabino and D-ribo configuration, respectively. © 1990.
引用
收藏
页码:1931 / 1942
页数:12
相关论文
共 21 条
  • [1] STEREOSELECTIVE SYNTHESIS OF TERT-BUTYL 2-AMINO-2,5-DIDEOXY-L-LYXO-PENTANOATE - FORMAL SYNTHESIS OF L-DAUNOSAMINE
    BANFI, L
    CARDANI, S
    POTENZA, D
    SCOLASTICO, C
    [J]. TETRAHEDRON, 1987, 43 (10) : 2317 - 2322
  • [2] ALPHA-AMINO POLYHYDROXY TETRONIC AND PENTONIC ACIDS FROM BROMODEOXYALDONOLACTONES .9.
    BOLS, M
    LUNDT, I
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (02): : 67 - 74
  • [3] HIGHLY STEREO AND REGIOCONTROLLED SYNTHESIS OF BOTH RACEMIC AND OPTICALLY-ACTIVE (-)-BLASTMYCINONE
    CARDELLACH, J
    FONT, J
    ORTUNO, RM
    [J]. TETRAHEDRON LETTERS, 1985, 26 (23) : 2815 - 2816
  • [4] ISOLATION OF GAMMA-HYDROXYNORVALINE FROM LATHYRUS ODORATUS SEED
    FOWDEN, L
    [J]. NATURE, 1966, 209 (5025) : 807 - &
  • [5] GREENSTEIN JP, 1961, CHEM AMINO ACIDS, V1, P3
  • [6] GUICHTER H, 1982, J ORG CHEM, V47, P2691
  • [7] Hunt S., 1985, CHEM BIOCH AMINO ACI, P55
  • [8] INTERPRETATION OF CONJUGATED OXIRANES BEHAVIOR TOWARD NUCLEOPHILES
    JAIME, C
    ORTUNO, RM
    FONT, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) : 139 - 141
  • [9] MARMAN TH, 1988, TETRAHEDRON LETT, V29, P1627
  • [10] MARNOKA K, 1985, CHEM LETT, P599