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
  • [31] SYNTHESIS AND FUNGICIDAL ACTIVITY OF SOME 2,4-DISUBSTITUTED THIAZOLES
    RAO, S
    MITTRA, AS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1977, 15 (11): : 1062 - 1063
  • [32] Synthesis and pharmacological evaluation of some 2,4-disubstituted hexahydroquinazolines
    Thangadurai, SA
    Kumar, BRA
    Ravi, TK
    Rajesh, R
    Rajasekaran, S
    Siddiqui, AA
    Alagarsamy, V
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2004, 14 (02) : 183 - 184
  • [33] Synthesis of 2,4-Disubstituted Imidazoles via Nucleophilic Catalysis
    Shabalin, Dmitrii A.
    Dunsford, Jay J.
    Ngwerume, Simbarashe
    Saunders, Alexandra R.
    Gill, Duncan M.
    Camp, Jason E.
    SYNLETT, 2020, 31 (08) : 797 - 800
  • [34] Synthesis of 2,4-disubstituted nortropinone derivatives by aldol condensation
    Jung, DI
    Park, CS
    Kim, YH
    Lee, DH
    Lee, YG
    Park, YM
    Choi, SK
    SYNTHETIC COMMUNICATIONS, 2001, 31 (21) : 3255 - 3263
  • [35] Facile Synthesis of 2,4-Disubstituted Thiooxazoles and 2,4-Disubstituted Oxazole Sulfonyl Chlorides via Acyl Isothiocyanates and TMS-Diazomethane
    Trujillo, John I.
    Arnold, Eric P.
    Kortum, Steve
    Robinson, Ralph P.
    SYNLETT, 2015, 26 (12) : 1764 - 1768
  • [36] PREPARATIONS OF 2,4-DISUBSTITUTED OESTRADIOLS
    PERT, DJ
    RIDLEY, DD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (03) : 421 - 432
  • [37] On the tautomerism of 2,4-disubstituted thiazolones
    Lin, YH
    Andersen, KK
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (03) : 557 - 563
  • [38] SYNTHESIS OF ADAMANTANE DERIVATIVES .50. FACILE SYNTHESIS OF 2,4-OXA-BRIDGED PROTOADAMANTANES AND THEIR CONVERSIONS TO 2-SUBSTITUTED AND 2,4-DISUBSTITUTED PROTOADAMANTANES AND A 2,4-DISUBSTITUTED ADAMANTANE
    SASAKI, T
    EGUCHI, S
    SUZUKI, T
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19): : 3824 - 3827
  • [39] Synthesis of Some New 2,4-Disubstituted Hydrazinothiazoles and 2,5-Disubstituted Thiazolidinones
    Manivel, P.
    Khan, F. Nawaz
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (11) : 2910 - 2922
  • [40] SYNTHESIS OF 1,2-DISUBSTITUTED AND 2,4-DISUBSTITUTED ADAMANTANES - PROTOADAMANTANE ROUTE
    LENOIR, D
    GLASER, R
    MISON, P
    SCHLEYER, PV
    JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (13): : 1821 - +