Recent developments in the synthesis of prostaglandins and analogues

被引:244
作者
Das, Saibal
Chandrasekhar, Srivari [1 ]
Yadav, Jhillu Singh
Gree, René
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
[2] Univ Rennes 1, Lab Synthese & Electrosynthese Organ, CNRS, UMR 6510, F-35042 Rennes, France
关键词
SELECTIVE EP4-RECEPTOR AGONIST; SOLID-PHASE SYNTHESIS; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; 2-COMPONENT COUPLING PROCESS; SILICON-CONTAINING COMPOUNDS; CLOSING ALKYNE METATHESIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; PROSTACYCLIN ANALOGS; METHYL-ESTER;
D O I
10.1021/cr068365a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recent developments in the synthesis of prostaglandins (PGs) and analogues were presented. Interesting and useful developments have been made by using new reagents and synthetic methodologies such as the metathesis reactions. Noteworthy also were the more systematic use of transition metal-mediated reactions, as well as enzymatic resolution methods. Development also included the synthesis of libraries of PGs by using a chemistry on support. In cyclopentenone PGs, syntheses involved cyclopentane derivatives as key intermediates and the use of retro-Diels Alder reactions. In the field of prostacyclin analogues, strategies have been introduced to obtain the desired optically active compounds by desymmetrization processes of key intermediates and to introduce efficiently the required ω-chain in the desired stereocenters. A large number of new analogues have been prepared for each series of Pgs in order to optimize biological activity.
引用
收藏
页码:3286 / 3337
页数:52
相关论文
共 218 条
  • [51] Palladium-catalyzed asymmetric synthesis of allylic alcohols from unsymmetrical and symmetrical racemic allylic carbonates featuring C-O-bond formation and dynamic kinetic resolution
    Gais, HJ
    Bondarev, O
    Hetzer, R
    [J]. TETRAHEDRON LETTERS, 2005, 46 (37) : 6279 - 6283
  • [52] Gais HJ, 1997, LIEBIGS ANN-RECL, P2419
  • [53] Prostaglandin E2-bisphosphonate conjugates:: Potential agents for treatment of osteoporosis
    Gil, L
    Han, YX
    Opas, EE
    Rodan, GA
    Ruel, R
    Seedor, JG
    Tyler, PC
    Young, RN
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (05) : 901 - 919
  • [54] Tandem Mukaiyama Michael-aldol reactions catalysed by samarium diiodide
    Giuseppone, N
    Collin, J
    [J]. TETRAHEDRON, 2001, 57 (43) : 8989 - 8998
  • [55] TRIPLY CONVERGENT SYNTHESIS OF 15-(PHENOXYMETHYL) AND 4,5-ALLENYL PROSTAGLANDINS - PREPARATION OF AN INDIVIDUAL ISOMER OF ENPROSTIL
    GOODING, OW
    BEARD, CC
    COOPER, GF
    JACKSON, DY
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) : 3681 - 3686
  • [56] An efficient synthesis of 3-hetero-13,14-dihydro prostaglandin F1α analogues
    Gu, JX
    Dirr, MJ
    Wang, YL
    Soper, DL
    De, B
    Wos, JA
    Johnson, CR
    [J]. ORGANIC LETTERS, 2001, 3 (05) : 791 - 794
  • [57] 3-oxa-15-cyclohexyl prostaglandin DP receptor agonists as topical antiglaucoma agents
    Hellberg, MR
    Conrow, RE
    Sharif, NA
    McLaughlin, MA
    Bishop, JE
    Crider, JY
    Dean, WD
    DeWolf, KA
    Pierce, DR
    Sallee, VL
    Selliah, RD
    Severns, BS
    Sproull, SJ
    Williams, GW
    Zinke, PW
    Klimko, PG
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (06) : 2031 - 2049
  • [58] A convenient synthesis of the beraprost intermediate: A useful method for introducing a C3 unit at the benzyl position
    Higuchi, K
    Sawada, K
    Nambu, H
    Shogaki, T
    Kita, Y
    [J]. ORGANIC LETTERS, 2003, 5 (20) : 3703 - 3704
  • [59] Prostaglandin D2 selectively induces chemotaxis in T helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2
    Hirai, H
    Tanaka, K
    Yoshie, O
    Ogawa, K
    Kenmotsu, K
    Takamori, Y
    Ichimasa, M
    Sugamura, K
    Nakamura, M
    Takano, S
    Nagata, K
    [J]. JOURNAL OF EXPERIMENTAL MEDICINE, 2001, 193 (02) : 255 - 261
  • [60] Enantioselective desymmetrisation of achiral epoxides
    Hodgson, DM
    Gibbs, AR
    Lee, GP
    [J]. TETRAHEDRON, 1996, 52 (46) : 14361 - 14384