A SHORT AND HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (3R,5R,8AR)-3-N-BUTYL-5-METHYLINDOLIZIDINE

被引:19
|
作者
CELIMENE, C [1 ]
DHIMANE, H [1 ]
LEBAIL, M [1 ]
LHOMMET, G [1 ]
机构
[1] UNIV PARIS 06, CNRS, CHIM HETEROCYCLES LAB, F-75252 PARIS, FRANCE
关键词
D O I
10.1016/0040-4039(94)88087-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of (-) (3R,5R,8aR)-3-n-Butyl-5-methylindolizidine is described in 9 steps (22% overall yield) from L-proline.
引用
收藏
页码:6105 / 6106
页数:2
相关论文
共 50 条
  • [31] NEW ALKALOIDS FROM ANTS - IDENTIFICATION AND SYNTHESIS OF (3R,5S,9R)-3-BUTYL-5-(1-OXOPROPYL)INDOLIZIDINE AND (3R,5R,9R)-3-BUTYL-5-(1-OXOPROPYL)INDOLIZIDINE, CONSTITUENTS OF THE POISON GLAND SECRETION IN MYRMICARIA-EUMENOIDES (HYMENOPTERA, FORMICIDAE)
    FRANCKE, W
    SCHRODER, F
    WALTER, F
    SINNWELL, V
    BAUMANN, H
    KAIB, M
    [J]. LIEBIGS ANNALEN, 1995, (06): : 965 - 977
  • [32] Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydro-furan-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate
    Punzo, F
    Cowley, AR
    Watkin, DJ
    Simone, MI
    Edwards, AA
    Tranter, GE
    Fleet, GWJ
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O473 - O475
  • [33] A SHORT, EFFICIENT SYNTHESIS OF (1S,3S,5R) AND (1S,3R,5R)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]-GNONANE
    BERNARDI, R
    GHIRINGHELLI, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22): : 5021 - 5022
  • [34] (2S,3R,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)proline]
    Best, Daniel
    Jenkinson, Sarah F.
    Thompson, Amber L.
    Watkin, David J.
    Wilson, Francis X.
    Nash, Robert J.
    Fleet, George W. J.
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2418 - +
  • [35] Synthesis of enantiomerically pure (3R,4R,5R)-4-hydroxy isoleucine lactone
    Kassem, T
    Wehbe, J
    Rolland-Fulcrand, V
    Rolland, M
    Roumestant, ML
    Martinez, J
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (19) : 2657 - 2661
  • [36] SYNTHESIS, ABSOLUTE-CONFIGURATION, AND STEREOCHEMISTRY OF THERMAL-DECOMPOSITION OF (+)-(3R,5R)-3-ETHYL-5-METHYL-1-PYRAZOLINES AND (+)-(3R,5S)-3-ETHYL-5-METHYL-1-PYRAZOLINES
    CLARKE, TC
    WENDLING, LA
    BERGMAN, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) : 5638 - 5640
  • [37] ASYMMETRIC-SYNTHESIS .3. ENANTIOSPECIFIC SYNTHESIS OF THE NATURAL 3R, 5R, 9R (-) GEPHYROTOXIN-223 AB
    ROYER, J
    HUSSON, HP
    [J]. TETRAHEDRON LETTERS, 1985, 26 (12) : 1515 - 1518
  • [38] Diastereoselective total synthesis of piperidine alkaloids: (2R,5R)-5-hydroxyhomopipecolic acid and (2R,5R,8R)-5-hydroxysedamine
    Khobare, Sandip R.
    Gajare, Vikas S.
    Rajana, Nagaraju
    Datrika, Rajender
    Reddy, K. Srinivasa
    Kumar, U. K. Syam
    Siddaiah, Vidavalur
    [J]. TETRAHEDRON LETTERS, 2015, 56 (17) : 2207 - 2210
  • [39] The first stereo selective total synthesis of (3R),(5R)-5-hydroxy-de-O-methyllasiodiplodin and its epimer via a RCM protocol
    Yadav, J. S.
    Das, Saibal
    Reddy, J. Satyanarayana
    Thrimurtulu, N.
    Prasad, A. R.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (31) : 4050 - 4052
  • [40] New developments in the asymmetric synthesis of (3R, 5R)-3,5-dihydroxyl-6-substituted hexanoic acid
    Chen, WS
    Chen, ZR
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (02) : 140 - 149