Synthesis of the 1,2,4-Thiadiazole Alkaloid Polyaurine B

被引：12
|
作者：
Anstis, Daniel G. [1 ]
Lindsay, Ashley C. [1 ]
Sohnel, Tilo [1 ]
Sperry, Jonathan [1 ]
机构：
[1] Univ Auckland, Sch Chem Sci, Auckland 1010, New Zealand
来源：
JOURNAL OF NATURAL PRODUCTS | 2020年 / 83卷 / 05期
关键词：
ROOT;
D O I：
10.1021/acs.jnatprod.0c00166
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
A short synthesis of the natural product polyaurine B is described. The 1,2,4-thiadiazole heterocycle was assembled using a Cu(II)-mediated heterocyclization reaction that forges the N-S bond. The final acylation step to install the methylcarbamate must be conducted under anhydrous, nonbasic conditions to prevent thiadiazole ring opening initiated by attack of hydroxide at C-5.
引用
收藏
页码：1721 / 1724
页数：4
相关论文
共 50 条
  • [1] Synthesis of the 1,2,4-thiadiazole alkaloids polycarpathiamines A and B
    Davison, Emma K.
    Sperry, Jonathan
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (01): : 38 - 42
  • [2] SYNTHESIS OF CERTAIN 1,2,4-THIADIAZOLE NUCLEOSIDES
    REVANKAR, GR
    ROBINS, RK
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (01) : 169 - 170
  • [3] 1,2,4-thiadiazole: A novel Cathepsin B inhibitor
    Leung-Toung, R
    Wodzinska, J
    Li, WR
    Lowrie, J
    Kukreja, R
    Desilets, D
    Karimian, K
    Tam, TF
    BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (24) : 5529 - 5537
  • [4] Intermolecular 1,2,4-thiadiazole synthesisBiocatalysis
    Peter W. Seavill
    Nature Synthesis, 2025, 4 (4): : 411 - 411
  • [5] 1,2,4-Thiadiazole alkaloids - Isolation, biological activity and synthesis
    Anstis, Daniel G.
    Davison, Emma K.
    Sperry, Jonathan
    TETRAHEDRON, 2024, 150
  • [6] Synthesis and insecticidal activity of 1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives
    Suzuki, Jun
    Okamura, Daigo
    Gushikawa, Toru
    Hirai, Kenji
    Ando, Tetsu
    JOURNAL OF PESTICIDE SCIENCE, 2011, 36 (03) : 392 - 401
  • [7] 1,2,4-Thiadiazole derivatives of cytisine
    V. A. Saprykina
    V. I. Vinogradova
    R. F. Ambartsumova
    T. F. Ibragimov
    A. Sultankulov
    Kh. M. Shakhidoyatov
    Chemistry of Natural Compounds, 2004, 40 : 582 - 584
  • [8] 1,2,4-thiadiazole 4-oxides
    Konstantinova, LS
    Rakitin, OA
    Rees, CW
    Torroba, T
    White, AJP
    Williams, DJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (16): : 2243 - 2248
  • [9] 1,2,4-Thiadiazole 4-oxides
    Rakitin, OA
    Rees, CW
    Vlasova, OG
    CHEMICAL COMMUNICATIONS, 1996, (11) : 1273 - 1274
  • [10] Advances in the synthesis and recent therapeutic applications of 1,2,4-thiadiazole heterocycles
    Castro, A
    Castaño, T
    Encinas, A
    Porcal, W
    Gil, C
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) : 1644 - 1652
12345