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
  • [21] SYNTHESIS OF 2,4-DISUBSTITUTED BICYCLO[3.1.0]HEXANE DERIVATIVES
    HOFFMANN, RW
    FRICKEL, F
    BLATT, K
    CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (03): : 831 - 843
  • [22] An efficient synthesis of novel 2,4-disubstituted tetrahydroquinolines and quinolines
    Devakaram, Ruth
    Black, David StC
    Kumar, Naresh
    TETRAHEDRON LETTERS, 2012, 53 (18) : 2269 - 2272
  • [23] The application of vinamidinium salts to the synthesis of 2,4-disubstituted thiophenes
    Clemens, RT
    Smith, SQ
    TETRAHEDRON LETTERS, 2005, 46 (08) : 1319 - 1320
  • [24] SYNTHESIS OF 2,4-DISUBSTITUTED 1,3-SELENAZOLES
    COHEN, VI
    SYNTHESIS-STUTTGART, 1979, (01): : 66 - 67
  • [25] SYNTHESIS OF 2,4-DISUBSTITUTED PYRIMIDINES, POLYPYRIMIDINEDIYLS, AND ANNULATED PYRIMIDINES
    POTTS, KT
    CIPULLO, MJ
    RALLI, P
    THEODORIDIS, G
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25): : 4841 - 4843
  • [26] A modular approach toward the synthesis of 2,4-disubstituted pyridines
    Singha, Raju
    Dhara, Shubhendu
    Ray, Jayanta K.
    TETRAHEDRON LETTERS, 2013, 54 (36) : 4841 - 4843
  • [27] Efficient Synthesis of 2,4-Disubstituted Thiazoles Under Grinding
    Heravi, Majid M.
    Poormohammad, Nargess
    Beheshtiha, Yahia S.
    Baghernejad, Bita
    SYNTHETIC COMMUNICATIONS, 2011, 41 (04) : 579 - 582
  • [28] Synthesis of 2,4-Disubstituted Quinolines in Deep Eutectic Solvents
    Chen, Guoqing
    Xie, Zongbo
    Liu, Yishuai
    Meng, Jia
    Le, Zhanggao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (01) : 156 - 161
  • [29] Practical synthesis of 2,4-disubstituted resorcinol derivatives.
    Ceglia, SS
    Kress, MH
    McNamara, JM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U135 - U136
  • [30] Synthesis and Antimicrobial Activity of Novel 2,4-Disubstituted Thiazoles
    Tran Nguyen Minh An
    Lee, Kap Duk
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (18) : 10160 - 10164