ASYMMETRIC-SYNTHESIS OF 3S,4R-DIHYDROXYPYRROLIDINES BY REGIOSELECTIVE AND STEREOSELECTIVE HYDROXYLATION OF 4-OXOPROLINE ENOLATE

被引:31
作者
BLANCO, MJ [1 ]
SARDINA, FJ [1 ]
机构
[1] UNIV SANTIAGO DE COMPOSTELA,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN
关键词
D O I
10.1016/S0040-4039(00)74441-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short, efficient and stereoselective synthesis of enantiomerically pure (2R, 3S, 4R) 3,4-dihydroxy-2-hydroxymethylpyrrolidine, a galactosidase inhibitor, from 4-hydroxy-L-proline is presented. The key steps are the regio- and stereoselective hydroxylation of a 4-oxoproline enolate and the stereoselective reduction of the resulting ketoalcohol. An N-(9-phenylfluoren-9-yl) moiety is used not only as an N-protecting group but as a regio- and stereochemical control element as well.
引用
收藏
页码:8493 / 8496
页数:4
相关论文
共 32 条
  • [1] ENANTIOSELECTIVE SYNTHESIS OF SWAINSONINE, A TRIHYDROXYLATED INDOLIZIDINE ALKALOID
    ADAMS, CE
    WALKER, FJ
    SHARPLESS, KB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) : 420 - 422
  • [2] A CHIRAL SYNTHESIS OF SWAINSONINE FROM D-GLUCOSE
    ALI, MH
    HOUGH, L
    RICHARDSON, AC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (07) : 447 - 448
  • [3] SYNTHESIS FROM D-LYXONOLACTONE OF 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL, A GLUCOSIDASE INHIBITOR WITH INVITRO ANTIVIRAL ACTIVITY
    BEHLING, JR
    CAMPBELL, AL
    BABIAK, KA
    NG, JS
    MEDICH, J
    FARID, P
    FLEET, GWJ
    [J]. TETRAHEDRON, 1993, 49 (16) : 3359 - 3366
  • [4] BENET RB, 1989, J AM CHEM SOC, V111, P2580
  • [5] SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE
    CARPENTER, NM
    FLEET, GWJ
    DIBELLO, IC
    WINCHESTER, B
    FELLOWS, LE
    NASH, RJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (51) : 7261 - 7264
  • [6] ALPHA-ACYLAMINO RADICAL CYCLIZATIONS - APPLICATION TO THE SYNTHESIS OF (-)-SWAINSONINE
    DENER, JM
    HART, DJ
    RAMESH, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) : 6022 - 6030
  • [7] SYNTHESIS OF "1,4,6-TRIDEOXY-1,4-IMINO-D-MANNITOL - A POTENT ALPHA-MANNOSIDASE INHIBITOR
    EIS, MJ
    RULE, CJ
    WURZBURG, BA
    GANEM, B
    [J]. TETRAHEDRON LETTERS, 1985, 26 (44) : 5397 - 5398
  • [8] PYRROLIDINE AND HEXAHYDRO-1H-AZEPINE MIMICS OF THE FLAP UP MANNOSYL CATION
    FARR, RA
    HOLLAND, AK
    HUBER, EW
    PEET, NP
    WEINTRAUB, PM
    [J]. TETRAHEDRON, 1994, 50 (04) : 1033 - 1044
  • [9] POTENT COMPETITIVE-INHIBITION OF ALPHA-GALACTOSIDASE AND ALPHA-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS - SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL
    FLEET, GWJ
    NICHOLAS, SJ
    SMITH, PW
    EVANS, SV
    FELLOWS, LE
    NASH, RJ
    [J]. TETRAHEDRON LETTERS, 1985, 26 (26) : 3127 - 3130
  • [10] GARST ME, 1978, TETRAHEDRON LETT, P2671