Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine

被引：41
作者：
Lin, Shuangzheng [1 ,2 ]
Deiana, Luca [1 ,2 ]
Tseggai, Abrehet [1 ,2 ]
Cordova, Armando [1 ,2 ,3 ]
机构：
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
[2] Stockholm Univ, Berzelii Ctr EXSELENT, S-10691 Stockholm, Sweden
[3] Mid Sweden Univ, Dept Nat Sci Engn & Math, S-85170 Sundsvall, Sweden
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 02期
关键词：
Organocatalysis; Asymmetric catalysis; Multicomponent reactions; Total synthesis; Natural products; Alkaloids; ENANTIOSPECIFIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESES; PICTET-SPENGLER REACTION; INDOLE ALKALOIDS; FORMAL SYNTHESIS; ASYMMETRIC-SYNTHESIS; GENERAL-APPROACH; CONJUGATE ADDITION; DIMETHYL-SULFOXIDE; ALPHA PRODUCTION;
D O I：
10.1002/ejoc.201101296
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences.
引用
收藏
页码：398 / 408
页数：11
相关论文
共 117 条
  • [1] Organocatalytic Domino Reactions
    Alba, Andrea-Nekane
    Companyo, Xavier
    Viciano, Monica
    Rios, Ramon
    [J]. CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) : 1432 - 1474
  • [2] Enantioselective Formal Synthesis of (+)-Dihydrocorynantheine and (-)-Dihydrocorynantheol
    Amat, Mercedes
    Gomez Esque, Arantxa
    Escolano, Carmen
    Santos, Maria M. M.
    Molins, Elies
    Bosch, Joan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) : 1205 - 1211
  • [3] Anastas P.T., 2000, Green Chemistry: Theory and Practice, P135, DOI DOI 10.1021/OP000054T
  • [4] [Anonymous], 2006, ANGEW CHEM
  • [5] IPECACUANHA ALKALOIDS .2. THE STRUCTURE OF PROTOEMETINE AND A PARTIAL SYNTHESIS OF (-)-EMETINE
    BATTERSBY, AR
    HARPER, BJT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAY): : 1748 - 1753
  • [6] BATTERSBY AR, 1966, TETRAHEDRON LETT, P4965, DOI 10.1016/S0040-4039(00)90310-1
  • [7] ASYMMETRIC-SYNTHESIS OF THE CORYNANTHEINE ALKALOIDS VIA AN INTRAMOLECULAR BLAISE REACTION - (-)-CORYNANTHEIDOL AND (-)-DIHYDROCORYNANTHEOL
    BEARD, RL
    MEYERS, AI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2091 - 2096
  • [8] Phytochemistry - Ibuprofen-like activity in extra-virgin olive oil
    Beauchamp, GK
    Keast, RSJ
    Morel, D
    Lin, JM
    Pika, J
    Han, Q
    Lee, CH
    Smith, AB
    Breslin, PAS
    [J]. NATURE, 2005, 437 (7055) : 45 - 46
  • [9] Antiviral activity of seven iridoids, three saikosaponins and one phenylpropanoid glycoside extracted from Bupleurum rigidum and Scrophularia scorodonia
    Bermejo, P
    Abad, MJ
    Díaz, AM
    Fernández, L
    De Santos, J
    Sanchez, S
    Villaescusa, L
    Carrasco, L
    Irurzun, A
    [J]. PLANTA MEDICA, 2002, 68 (02) : 106 - 110
  • [10] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
    Brandau, Sven
    Landa, Aitor
    Franzen, Johan
    Marigo, Mauro
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
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