Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

被引:25
作者
Macha, Lingamurthy [1 ]
D'hooghe, Matthias [2 ]
Ha, Hyun-Joon [1 ]
机构
[1] Hankuk Univ Foreign Studies, Dept Chem, Yongin 17035, South Korea
[2] Univ Ghent, Fac Biosci Engn, Dept Green Chem & Technol, SynBioC Res Grp, Coupure Links 653, B-9000 Ghent, Belgium
来源
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 07期
基金
新加坡国家研究基金会;
关键词
aziridine; ring strain; iminosugars; alkaloids; natural products; DIMERIC SESQUITERPENE THIOALKALOIDS; PROTEIN-KINASE-C; PIPERIDINE ALKALOIDS; ASYMMETRIC-SYNTHESIS; POLYHYDROXYLATED PYRROLIDINE; ENANTIOSELECTIVE SYNTHESES; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; NUPHAR ALKALOIDS; FORMAL SYNTHESIS;
D O I
10.1055/s-0037-1611715
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various (activated and non-activated) aziridines with diverse substitution patterns have been deployed successfully as starting materials for the synthesis of a wide variety of alkaloids via suitable functionalization and aziridine ring transformation. Alternatively, the preparation and interception of reactive aziridine intermediates has also been shown to constitute a valid approach toward alkaloid synthesis. This review summarizes aziridine-mediated syntheses of alkaloids, in which the aziridine is mobilized as either a substrate or an advanced synthetic intermediate.
引用
收藏
页码:1491 / 1515
页数:25
相关论文
共 119 条
  • [51] AN ALKALOID WITH HIGH ANTIMALARIAL ACTIVITY FROM DICHROA-FEBRIFUGA
    KOEPFLI, JB
    MEAD, JF
    BROCKMAN, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (07) : 1837 - 1837
  • [52] USTILOXINS, ANTIMITOTIC CYCLIC-PEPTIDES FROM FALSE SMUT BALLS ON RICE PANICLES CAUSED BY USTILAGINOIDEA VIRENS
    KOISO, Y
    LI, Y
    IWASAKI, S
    HANAOKA, K
    KOBAYASHI, T
    SONODA, R
    FUJITA, Y
    YAEGASHI, H
    SATO, Z
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (07) : 765 - 773
  • [53] Enantioselective Construction of a Polyhydroxylated Pyrrolidine Skeleton from 3-Vinylaziridine-2-carboxylates: Synthesis of (+)-DMDP and a Potential Common Intermediate for (+)-Hyacinthacine A1 and (+)-1-epi-Australine
    Kondo, Yukari
    Suzuki, Noriyuki
    Takahashi, Masato
    Kumamoto, Takuya
    Masu, Hyuma
    Ishikawa, Tsutomu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18) : 7988 - 7999
  • [54] STRUCTURE OF A NEW PIPERIDINE DERIVATIVE FROM BUCKWHEAT SEEDS - FAGOPYRUM-ESCULENTUM MOENCH
    KOYAMA, M
    SAKAMURA, S
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1974, 38 (05): : 1111 - 1112
  • [55] Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities
    Kumar, K. S. Ajish
    Chaudhari, Vinod D.
    Dhavale, Dilip D.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (04) : 703 - 711
  • [56] A new route to spiropyrrolidinyl-oxindole alkaloids via iodide ion induced rearrangement of [(N-aziridinomethylthio)methylene]-2-oxindoles
    Kumar, UKS
    Ila, H
    Junjappa, H
    [J]. ORGANIC LETTERS, 2001, 3 (26) : 4193 - 4196
  • [57] Five new nortropane alkaloids and six new amino acids from the fruit of Morus alba LINNE growing in Turkey
    Kusano, G
    Orihara, S
    Tsukamoto, D
    Shibano, M
    Coskun, M
    Guvenc, A
    Erdurak, CS
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (02) : 185 - 192
  • [58] Stereoselective synthesis of (-)-8-epi-swainsonine starting with a chiral aziridine
    Lee, Baeck Kyoung
    Choi, Hwan Geun
    Roh, Eun Joo
    Lee, Won Koo
    Sim, Taebo
    [J]. TETRAHEDRON LETTERS, 2013, 54 (06) : 553 - 556
  • [59] Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine
    Lee, Hogyu
    Kim, Jun Hee
    Lee, Won Koo
    Cho, Jaeheung
    Nam, Wonwoo
    Lee, Jaedeok
    Ha, Hyun-Joon
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (22) : 3629 - 3634
  • [60] Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy
    Lee, Jisun
    Joullie, Madeleine M.
    [J]. CHEMICAL SCIENCE, 2018, 9 (09) : 2432 - 2436