Chemoenzymatic enantiodivergent synthesis of 1,2-dideoxy-2-amino-1-fluoro-allo-inositol.

被引：12
|
作者：
Oppong, KA [1 ]
Hudlicky, T [1 ]
Yan, FY [1 ]
York, CT [1 ]
Nguyen, BV [1 ]
机构：
[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 10期
基金：
美国国家科学基金会;
关键词：
biooxidation; enantioselectivity; fluoroamino inositols; toluene dioxygenase;
D O I：
10.1016/S0040-4020(99)00080-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (-)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through S(N)2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epoxide opening with tetrabutylphosphonium fluoride dihydrofluoride (TBPF-DF). (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2875 / 2880
页数：6
相关论文
共 50 条
  • [31] Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof
    Ziegler, T
    Bien, F
    Jurisch, C
    TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 765 - 780
  • [32] PRACTICAL EPC SYNTHESIS OF 1,2-AMINO AND 1,3-AMINO ALCOHOLS
    GMEINER, P
    KARTNER, A
    JUNGE, D
    TETRAHEDRON LETTERS, 1993, 34 (27) : 4325 - 4326
  • [33] AN ENANTIOSELECTIVE CHEMOENZYMATIC SYNTHESIS OF THE 4 1-AMINO 2-METHYLCYCLOPROPANE CARBOXYLIC-ACIDS
    DILUGANO, FR
    MONTEIRO, J
    FLICHE, C
    BRAUN, J
    LEGOFFIC, F
    SYNTHETIC COMMUNICATIONS, 1992, 22 (08) : 1155 - 1158
  • [34] Chemo-enzymatic synthesis of 2′,3′-dideoxy-3′-fluoro-β-D-guanosine via 2,3-dideoxy-3-fluoro-α-D-ribose 1-phosphate
    Komatsu, H
    Araki, T
    TETRAHEDRON LETTERS, 2003, 44 (14) : 2899 - 2901
  • [35] 2-OXAZOLIDINONES AS REGIOSELECTIVE PROTECTION OF BETA-AMINO ALCOHOLS IN THE SYNTHESIS OF 2-AMINO-1-ARYL-3-FLUORO-1-PROPANOLS
    JOMMI, G
    PAGLIARIN, R
    TAVECCHIA, P
    CHIARINO, D
    FANTUCCI, M
    GAZZETTA CHIMICA ITALIANA, 1986, 116 (09): : 485 - 489
  • [36] INOSITOL DERIVATIVES .4. SYNTHESIS OF ANHYDRO DERIVATIVES OF 1,2-O-CYCLOHEXYLIDENE-INOSITOL
    SUAMI, T
    OGAWA, S
    OKI, S
    OHASHI, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (08) : 2597 - +
  • [37] A new preparative synthesis of 1-D-6-O-(2-amino-2-deoxy-D-glycopyranosyl)-chiro-inositol 1-phosphate and 1,2-cyclic phosphate
    Martín-Lomas, M
    Flores-Mosquera, M
    Khiar, N
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (08) : 1539 - 1545
  • [38] Synthesis and preliminary biological evaluations of [18F]-1-deoxy-1-fluoro-scyllo-inositol
    Vasdev, Neil
    Chio, Jason
    van Oosten, Erik M.
    Nitz, Mark
    McLaurin, JoAnne
    Vines, Douglass C.
    Houle, Sylvain
    Reilly, Raymond M.
    Wilson, Alan A.
    CHEMICAL COMMUNICATIONS, 2009, (37) : 5527 - 5529
  • [39] Synthesis of optically pure 1,2-diaryl- and 1,2-alkylaryl-1,2-amino sulfides
    Arroyo, Y
    Meana, A
    Rodríguez, JF
    Santos, M
    Sanz-Tejedor, MA
    Ruano, JLG
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10): : 3914 - 3920
  • [40] Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks (vol 8, pg 751, 2010)
    Austin, Kerrie A. B.
    Elsworth, Jon D.
    Banwell, Martin G.
    Willis, Anthony C.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (24) : 8504 - 8504
12345