Enantioselective synthesis of 2-[(3-ethyl-4-piperidyl)methyl]indoles from a phenylglycinol-derived lactam:: formal synthesis of Strychnos alkaloids

被引：9
作者：
Amat, Mercedes [1 ]
Llor, Nuria [1 ]
Checa, Begona [1 ]
Perez, Maria [1 ]
Bosch, Joan [1 ]
机构：
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 38期
关键词：
phenylglycinol; Strychnos alkaloids; piperidines; indoles; oxazolopiperidone lactams;
D O I：
10.1016/j.tetlet.2007.07.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A diastereodivergent synthesis of enantiopure cis- and traiis-2-[(3-ethyl-4-piperidyl)methyl]indole (cis-1b and trans-1b) from a common phenylglycino]-derived oxazolopiperidone lactam 3 is reported. The key step is a stereocontrolled conjugate addition, either under kinetic or thermodynamic control, of the dilithium salt of 2-(2-indolyl)-1,3-dithiane to unsaturated lactam 3. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6722 / 6725
页数：4
相关论文
共 35 条
  • [1] Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets
    Allin, Steven M.
    Duffy, Liam J.
    Bulman Page, Philip C.
    McKee, Vickie
    Edgar, Mark
    McKenzie, Michael J.
    Amat, Mercedes
    Bassas, Oriol
    Santos, Maria M. M.
    Bosch, Joan
    [J]. TETRAHEDRON LETTERS, 2006, 47 (32) : 5713 - 5716
  • [2] ALVAREZ M, 1994, MONOTERPENOID IN 4 S, V25, pCH6
  • [3] ALVAREZ M, 2001, ALKALOIDS, V57, pCH4
  • [4] Alkylation of phenylglycinol-derived oxazolopiperidone lactams.: Enantioselective synthesis of β-substituted piperidines
    Amat, M
    Escolano, C
    Lozano, O
    Gomez-Esque, A
    Griera, R
    Molins, E
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10) : 3804 - 3815
  • [5] Conjugate additions to phenylglycinol-derived unsaturated δ-lactams.: Enantioselective synthesis of uleine alkaloids
    Amat, M
    Pérez, M
    Llor, N
    Escolano, C
    Luque, FJ
    Molins, E
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (25) : 8681 - 8693
  • [6] Conjugate addition of organocuprates to chiral bicyclic δ-lactams.: Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines
    Amat, M
    Pérez, M
    Llor, N
    Bosch, J
    Lago, E
    Molins, E
    [J]. ORGANIC LETTERS, 2001, 3 (04) : 611 - 614
  • [7] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine
    Amat, M
    Bosch, J
    Hidalgo, J
    Cantó, M
    Pérez, M
    Llor, N
    Molins, E
    Miravitlles, C
    Orozco, M
    Luque, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3074 - 3084
  • [8] Total syntheses of the Strychnos indole alkaloids (-)-tubifoline, (-)-tubifolidine, and (-)-19,20-dihydroakuammicine
    Amat, M
    Coll, MD
    Bosch, J
    Espinosa, E
    Molins, E
    [J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (06) : 935 - 948
  • [9] AMAT M, 2007, TETRAHEDRON-ASYMMETR, V72, P4431
  • [10] A general synthetic route to enantiopure cis-fused perhydrocycloalka[c]pyridines from phenylglycinol-derived lactams
    Amat, Mercedes
    Perez, Maria
    Minaglia, Annamaria T.
    Peretto, Bruno
    Bosch, Joan
    [J]. TETRAHEDRON, 2007, 63 (26) : 5839 - 5848
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