Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine

被引：42
作者：
Kitajima, Mariko [1 ]
Watanabe, Keisuke [1 ]
Maeda, Hiroyuki [1 ]
Kogure, Noriyuki [1 ]
Takayama, Hiromitsu [1 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 08期
关键词：
ENANTIOSPECIFIC TOTAL-SYNTHESIS; STEREOSPECIFIC TOTAL-SYNTHESIS; BIOMIMETIC SYNTHESIS; ABSOLUTE-CONFIGURATION; GELSEMIUM ALKALOIDS; FORMAL SYNTHESES; SKELETON; P-(+)-DISPEGATRINE; (-)-TABERPSYCHINE; (-)-KOUMIDINE;
D O I：
10.1021/acs.orglett.6b00661
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sarpagine-related indole alkaloids (-)-hydroxygardnerine, (+)-hydroxygardnutine, (+)-gardnerine, (+)-(E)-16-epi-normacusine B, and (-)-koumine were divergently synthesized via a common intermediate possessing a piperidine ring with an exocyclic (E)-ethylidene side chain, which was constructed by a gold(I)-catalyzed 6-exo-dig cyclization strategy.
引用
收藏
页码：1912 / 1915
页数：4
相关论文
共 35 条
  • [1] Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A
    Adams, Gregory L.
    Carroll, Patrick J.
    Smith, Amos B., III
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (01) : 519 - 528
  • [2] AIMI N, 1978, CHEM PHARM BULL, V26, P3444
  • [3] USE OF THE KINETICALLY CONTROLLED PICTET-SPENGLER REACTION IN THE ASYMMETRIC-SYNTHESIS OF INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-AJMALINE, (-)-KOUMINE, (-)-TABERPSYCHINE, (-)-KOUMIDINE AND (-)-SUAVOLINE
    BAILEY, PD
    MCLAY, NR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04): : 441 - 449
  • [4] ASYMMETRIC-SYNTHESIS OF INDOLE ALKALOIDS FROM (L)-TRYPTOPHAN - FORMAL SYNTHESES OF (-)-KOUMINE, (-)-TABERPSYCHINE AND (-)-KOUMIDINE
    BAILEY, PD
    MCLAY, NR
    [J]. TETRAHEDRON LETTERS, 1991, 32 (31) : 3895 - 3898
  • [5] Synthesis, Enantiomer Separation, and Absolute Configuration of 2,6-Oxygenated 9-Azabicyclo[3.3.1]nonanes
    Bieliunas, Vidmantas
    Rackauskaite, Dovile
    Orentas, Edvinas
    Stoncius, Sigitas
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11) : 5339 - 5348
  • [6] ALKALOIDS FROM LEAVES AND ROOT BARK OF ERVATAMIA-HIRTA
    CLIVIO, P
    RICHARD, B
    DEVERRE, JR
    SEVENET, T
    ZECHES, M
    LEMENOLIVER, L
    [J]. PHYTOCHEMISTRY, 1991, 30 (11) : 3785 - 3792
  • [7] Synthesis and structural characterization of N-heterocyclic carbene gold(I) complexes
    de Frémont, P
    Scott, NM
    Stevens, ED
    Nolan, SP
    [J]. ORGANOMETALLICS, 2005, 24 (10) : 2411 - 2418
  • [8] Stereospecific Approach to the Synthesis of Ring-A Oxygenated Sarpagine Indole Alkaloids. Total Synthesis of the Dimeric Indole Alkaloid P-(+)-Dispegatrine and Six Other Monomeric Indole Alkaloids
    Edwankar, Chitra R.
    Edwankar, Rahul V.
    Namjoshi, Ojas A.
    Liao, Xuebin
    Cook, James M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13) : 6471 - 6487
  • [9] Nature-Inspired Stereospecific Total Synthesis of P-(+)-Dispegatrine and Four Other Monomeric Sarpagine Indole Alkaloids
    Edwankar, Chitra R.
    Edwankar, Rahul V.
    Deschamps, Jeffrey R.
    Cook, James M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (47) : 11762 - 11765
  • [10] General Strategy for Synthesis of C-19 Methyl-Substituted Sarpagine/Macroline/Ajmaline Indole Alkaloids Including Total Synthesis of 19(S),20(R)-Dihydroperaksine, 19(S),20(R)-Dihydroperaksine-17-al, and Peraksine
    Edwankar, Rahul V.
    Edwankar, Chitra R.
    Deschamps, Jeffrey R.
    Cook, James M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10030 - 10048
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