Intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives towards novel heterocyclic scaffolds

被引：20
|
作者：
Fischer, Thomas C. M. [1 ]
Leisch, Hannes G. [1 ]
Mihovilovic, Marko D. [1 ]
机构：
[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
来源：
MONATSHEFTE FUR CHEMIE | 2010年 / 141卷 / 06期
关键词：
Bioorganic chemistry; Cycloadditions; Enzymes; Biosynthesis; Dioxygenases; CHEMOENZYMATIC TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; DIHYDROXYLATION; REARRANGEMENT; ROUTE;
D O I：
10.1007/s00706-010-0291-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The potential of biodihydroxylated benzoic acid derivatives as versatile precursors for the construction of polycyclic scaffolds was investigated. Ralstonia eutropha B9 was used to biodihydroxylate sodium benzoate to sodium (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate in high optical purity (>95% ee). The required cyclization precursors could be obtained in moderate to excellent yields after protection of the intermediate and subsequent functional group transformation. Intramolecular Diels-Alder cylizations were carried out under thermal or microwave conditions leading to enantiomerically pure products with five chiral centers.
引用
收藏
页码：699 / 707
页数：9
相关论文
共 50 条
  • [31] An intramolecular Diels-Alder approach to the spirotetronic acid subunits of the quartromicins
    Roush, WR
    Barda, DA
    TETRAHEDRON LETTERS, 1997, 38 (51) : 8781 - 8784
  • [32] HYDROFLUORIC-ACID CATALYZED INTRAMOLECULAR DIELS-ALDER REACTIONS
    ROUSH, WR
    GILLIS, HR
    ESSENFELD, AP
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24): : 4674 - 4682
  • [33] Diels-Alder polymerization of some derivatives of abietic acid
    Bicu, I
    Mustata, F
    ANGEWANDTE MAKROMOLEKULARE CHEMIE, 1999, 264 : 21 - 29
  • [34] Intramolecular Diels-Alder Reaction of Cyclopropenyl Vinylarenes: Access to Benzonorcarane Derivatives
    Martinez, Angel Manu
    Puet, Alejandro
    Dominguez, Gema
    Alonso, Ines
    Castro-Biondo, Rodrigo
    Perez-Castells, Javier
    ORGANIC LETTERS, 2023, 25 (32) : 5923 - 5928
  • [35] Fluorogenic Diels-Alder reactions of novel phencyclone derivatives
    Aydin, Engin Aytac
    Altenbach, Hans-Josef
    TETRAHEDRON LETTERS, 2013, 54 (14) : 1832 - 1834
  • [36] DIELS-ALDER REACTION OF CINNAMIC ACID DERIVATIVES WITH CYCLOPENTADIENE
    RONDESTVEDT, CS
    VERNOOY, CD
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (18) : 4878 - 4883
  • [37] Diastereoselective intramolecular hetero Diels-Alder approach towards polycyclic heterocycles
    Ceulemans, E
    Voets, M
    Emmers, S
    Uytterhoeven, K
    Van Meervelt, L
    Dehaen, W
    TETRAHEDRON, 2002, 58 (03) : 531 - 544
  • [38] INTRAMOLECULAR DIELS-ALDER CYCLOADDITION OF ISOXAZOLE DERIVATIVES CATALYZED BY BRONSTED ACIDS
    BRANDI, A
    NUTI, P
    HETEROCYCLES, 1987, 26 (01) : 47 - 50
  • [39] INTRAMOLECULAR AND INTERMOLECULAR DIELS-ALDER ADDUCTS FROM SORBIC ALDEHYDE DERIVATIVES
    EBERLE, MK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 185 (MAR): : 215 - ORGN
  • [40] ACID-CATALYZED INTRAMOLECULAR 2-AZA-1,3-DIENE DIELS-ALDER CYCLIZATION PROCESSES
    HO, E
    CHENG, YS
    MARIANO, PS
    TETRAHEDRON LETTERS, 1988, 29 (38) : 4799 - 4802
12345