STEREOSELECTIVE SYNTHESIS OF THE TRANS 2,4-DISUBSTITUTED BUTYROLACTONE MOIETY OF ANNONACEOUS ACETOGENINS

被引:0
|
作者
BERTRAND, P [1 ]
GESSON, JP [1 ]
机构
[1] LAB CHIM 12,URA 1468,40 AVE RECTEUR PINEAU,F-86022 POITIERS,FRANCE
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective preparation of the trans 2-alkyl-4-acetonylbutyrolactone moiety present in some bioactive mono or bis-tetrahydrofuran acetogenins has been carried out from glycidol tosylate using two consecutive alkylations. The formation of a methyl pyranoside from the intermediate mixture of epimeric cyano alcohols allows control of the relative 1,3-configurations before lactonization.
引用
收藏
页码:889 / 890
页数:2
相关论文
共 50 条
  • [41] Chemoenzymatic Synthesis of trans-Tetrahydrofuran Cores of Annonaceous Acetogenins from Bromobenzene
    Carlos Ramos, Juan
    Brovetto, Margarita
    Seoane, Gustavo A.
    ORGANIC LETTERS, 2013, 15 (08) : 1982 - 1985
  • [42] NOVEL CYTOTOXIC ANNONACEOUS ACETOGENINS - (2,4-CIS AND TRANS)-BULLADECINONES FROM ANNONA-BULLATA (ANNONACEAE)
    GU, ZM
    FANG, XP
    ZENG, L
    KOZLOWSKI, JF
    MCLAUGHLIN, JL
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (03) : 473 - 478
  • [43] Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines
    Mehton, Ramandeep K.
    Meshram, Vineet
    Saxena, Sanjai
    Chhibber, Manmohan
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2016, 27 (07) : 1236 - 1244
  • [44] SYNTHESIS AND RADIOCHEMISTRY OF 2,4-DISUBSTITUTED 17-ALPHA-IODOVINYLESTRADIOLS
    CUMMINS, CH
    STEROIDS, 1994, 59 (10) : 590 - 596
  • [45] Synthesis, Anticancer and Antioxidant Activity of Novel 2,4-Disubstituted Thiazoles
    Tran Nguyen Minh An
    Kumar, Mungara Anil
    Chang, Seung Hyun
    Kim, Mi Yeong
    Kim, Jung-Ae
    Lee, Kap Duk
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (06): : 1619 - 1624
  • [46] Synthesis, Antibacterial Activity of 2,4-Disubstituted Oxazoles and Thiazoles as Bioisosteres
    Kaspady, Mohamed
    Narayanaswamy, Venugopala Katharigatta
    Raju, Mohana
    Rao, Gopal Krishna
    LETTERS IN DRUG DESIGN & DISCOVERY, 2009, 6 (01) : 21 - 28
  • [47] A diastereoselective synthesis of 2,4-disubstituted piperidines: Scaffolds for drug discovery
    Watson, PS
    Jiang, B
    Scott, B
    ORGANIC LETTERS, 2000, 2 (23) : 3679 - 3681
  • [48] Design, synthesis and evaluation of 2,4-disubstituted pyrimidines as cholinesterase inhibitors
    Mohamed, Tarek
    Rao, Praveen P. N.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (12) : 3606 - 3609
  • [49] NOVEL SYNTHESIS OF 2,4-DISUBSTITUTED DIHYDRO-NU-TRIAZOLES
    REDDY, PA
    SINGH, S
    SRINIVASAN, VR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1976, 14 (10): : 793 - 794
  • [50] Synthesis and anti-tuberculosis activity of 2,4-disubstituted quinolines
    Nayyart, Amit
    Jain, Rahul
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (01): : 117 - 128