A new synthetic route to β-unsubstituted β-lactones by intramolecular cyclization

被引:8
作者
Alexandre, FR [1 ]
Legoupy, S [1 ]
Huet, F [1 ]
机构
[1] Univ Maine, Organ Synth Lab, UPRES A CNRS 6011, Fac Sci, F-72085 Le Mans 9, France
关键词
beta-lactones; cyclization; reduction; enzymatic hydrolysis;
D O I
10.1016/S0040-4020(00)00313-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
When carboxylic acids beta-substituted by a tert-butoxy group were treated with thionyl chloride, an intermediate acyl chloride beta-substituted by a hydroxyl group was likely formed. Its subsequent intramolecular cyclization produced novel beta-lactones in one step. Two enantiomerically enriched lactones could be prepared via intermediates obtained by enzymatic hydrolysis. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3921 / 3926
页数:6
相关论文
共 26 条
  • [11] SYNTHESIS AND POLYMERIZATION OF RACEMIC AND OPTICALLY-ACTIVE SUBSTITUTED BETA-PROPIOLACTONES .5. ALPHA-METHYL BETA-PROPIOLACTONE
    HMAMOUCHI, M
    PRUDHOMME, RE
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1988, 26 (06) : 1593 - 1607
  • [12] ENZYME-CATALYZED HYDROLYSIS OF SOME FUNCTIONALIZED DIMETHYL MALONATES
    LUYTEN, M
    MULLER, S
    HERZOG, B
    KEESE, R
    [J]. HELVETICA CHIMICA ACTA, 1987, 70 (05) : 1250 - 1254
  • [13] STEREOSPECIFIC ROUTE TO TRISUBSTITUTED OLEFINS VIA BETA-LACTONES
    MAGESWARAN, S
    SULTANBAWA, MUS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (08): : 884 - 890
  • [14] Enterobactin and enantioenterobactin
    Marinez, ER
    Salmassian, EK
    Lau, TT
    Gutierrez, CG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) : 3548 - 3550
  • [15] MULZER J, 1991, COMPREHENSIVE ORGANI, V6, P342
  • [16] SYNTHESIS OF (-)-NORANISATIN, AN OXIDATION-PRODUCT OF A NEUROTOXIC SESQUITERPENOID ANISATIN HAVING A NOVEL SPIRO BETA-LACTONE
    NIWA, H
    ITO, S
    HASEGAWA, T
    WAKAMATSU, K
    MORI, T
    YAMADA, K
    [J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1329 - 1330
  • [17] SYNTHESIS OF AN ISOSTERIC PHOSPHONATE ANALOG OF CYTIDINE 5'-MONOPHOSPHO-3-DEOXY-D-MANNO-2-OCTULOSONIC ACID
    NORBECK, DW
    KRAMER, JB
    LARTEY, PA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) : 2174 - 2179
  • [18] PECQUET P, 1992, HETEROCYCLES, V34, P739
  • [19] POMMIER A, 1993, SYNTHESIS-STUTTGART, P441
  • [20] MECHANISM OF FORMATION OF SERINE BETA-LACTONES BY MITSUNOBU CYCLIZATION - SYNTHESIS AND USE OF L-SERINE STEREOSPECIFICALLY LABELED WITH DEUTERIUM AT C-3
    RAMER, SE
    MOORE, RN
    VEDERAS, JC
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (04): : 706 - 713