MACROCYCLIC LACTONIZATION OF 3R,7-DIMETHYL-6S-HYDROXYOCTANOIC ACID

被引:1
|
作者
Yakovleva, M. P. [1 ]
Mingaleeva, G. R. [1 ]
Denisova, K. S. [1 ]
Kravchenko, A. A. [1 ]
Vyrypaev, E. M. [1 ]
Ishmuratov, G. Yu [1 ]
机构
[1] Russian Acad Sci, Ufa Inst Chem, 71 Prosp Oktyabrya, Ufa 450054, Russia
关键词
1-menthol; 3R; 7-dimethyl-6S-hydroxyoctanoic acid; dicarboxylic acid dichlorides; pyridine; N; N-dimethylaminopyridine;
D O I
10.1007/s10600-018-2446-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A mixture of cyclic lactones [7- (mentholactone), 14-, 21-, 28-, and 35-membered polylactones] instead of the expected [2 + 1]-condensation products was obtained from the reaction of 3R, 7-dimethyl-6S-hydroxyoctanoic acid, which is accessible from l-menthol, and glutaric, adipic, and bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dichlorides in Py in the presence of N,N-dimethylaminopyridine. The structures were confirmed using PMR, C-13 NMR, and mass spectra.
引用
收藏
页码:684 / 687
页数:4
相关论文
共 50 条
  • [41] (2R,3R)-diacetyltartaric acid anhydride
    Qi, ZB
    Zhang, MJ
    Yuan, DY
    Ma, SS
    Wang, XQ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1085 - O1086
  • [42] (1S,3R,6S)-3-Chloro-trans-himachalene
    Benharref, Ahmed
    Mazoir, Noureddine
    Moha, Berraho
    Essediya, Lassaba
    Daran, Jean-Claude
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O3681 - U1904
  • [43] CONVENIENT HIGHLY STEREOSELECTIVE SYNTHESES OF (3R,7R,11R) AND (3S,7R,11R)-3,7,11,15-TETRAMETHYLHEXADECANOIC ACID (PHYTANIC ACID) AND THE CORRESPONDING 3,7,11,15-TETRAMETHYLHEXADECAN-1-OLS
    SITA, LR
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19): : 5285 - 5287
  • [44] Synthesis and configuration of (1S,3R)- and (1R,3R)-1-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,3-dihydroisobenzofurans
    Shishkina, Irina N.
    Demyanovich, Valeriya M.
    Potekhin, Konstantin A.
    Gurbanov, Atash V.
    Zefirov, Nikolay S.
    MENDELEEV COMMUNICATIONS, 2015, 25 (01) : 11 - 12
  • [45] THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
    BASHYAL, BP
    CHOW, HF
    FELLOWS, LE
    FLEET, GWJ
    TETRAHEDRON, 1987, 43 (02) : 415 - 422
  • [46] Synthesis of (3R,5R)-harzialactone A and its (3R,5S)-isomer
    Sabitha, Gowravaram
    Srinivas, Rangavajjula
    Das, Sukant K.
    Yadav, Jhillu S.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6
  • [47] Total Synthesis of (3R,3′R,6′R)-Lutein and Its Stereoisomers
    Khachik, Frederick
    Chang, An-Ni
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3875 - 3885
  • [48] (3R,6R)-3,4-DIMETHYL-1,4-DIAZABICYCLO[4.4.0]DECANE-2,5-DIONE
    VERBRUGGEN, M
    LENSTRA, ATH
    REYNIERS, F
    BORREMANS, F
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 1113 - 1116
  • [49] SYNTHESIS (2S, 3R, 4R, 6E)-3-HYDROXY-4-METHYL-2-METHYLAMINO-6-OCTENIC ACID
    OGORODNICHUK, AS
    DYBENKO, AG
    ROMANOVA, VP
    SHILIN, VV
    UKRAINSKII KHIMICHESKII ZHURNAL, 1990, 56 (11): : 1203 - 1205
  • [50] THE SYNTHESIS OF (2R,3S)-(2S,3R) [4-C-14]AGARIC ACID AND (2R,3R)-(2S-3S) [4,4,5,5-H-3]AGARIC ACID
    LELLOUCHE, JP
    BEAUCOURT, JP
    PICHAT, L
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1984, 21 (02): : 125 - 132