Synthesis of the ester side chains of homoharringtonine and harringtonine using lactones as building blocks

被引:3
|
作者
Dang, Fang-Fang [1 ]
Wang, Cui-Cui [2 ]
Han, Feng [3 ]
Zhang, Zhi-Wei [2 ]
机构
[1] Xian Univ Architecture & Technol, Sch Chem & Chem Engn, Xian, Peoples R China
[2] Hebei Univ Sci & Technol, Coll Chem & Pharmaceut Engn, Yuxiang Rd 26, Shijiazhuang 050018, Hebei, Peoples R China
[3] CSPC Innovat Pharmaceut Co Ltd, Shijiazhuang, Hebei, Peoples R China
关键词
Alkaloid; classic reactions; efficient synthesis; ester side chain; homoharringtonine; ENANTIOSELECTIVE SYNTHESIS; REARRANGEMENT; ALKALOIDS;
D O I
10.1080/00397911.2020.1829643
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient synthesis of the ester side chains of homoharringtonine and harringtonine using lactones as building blocks has been developed. The synthesis used classic reactions from readily available starting materials. Reactions of the lactone bearing an oxo-containing alpha-tetrasubstituted center with MeOH and cephalotaxine, respectively, proceeded smoothly to give the corresponding ring-opening products in 80% and 65% yield.
引用
收藏
页码:317 / 323
页数:7
相关论文
共 50 条
  • [31] BUILDING-BLOCKS OF OLIGOSACCHARIDES .75. THE SYNTHESIS OF HEXAPEPTIDE SEQUENCE-43-TO-48 OF ASIALOGLYCOPHORIN-A WITH 2 DISACCHARIDE SIDE-CHAINS
    PAULSEN, H
    SCHULTZ, M
    CARBOHYDRATE RESEARCH, 1987, 159 (01) : 37 - 52
  • [32] Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks
    Davis, FA
    Chao, B
    Andemichael, YW
    Mohanty, PK
    Fang, TN
    Burns, DM
    Rao, A
    Szewczyk, JM
    HETEROATOM CHEMISTRY, 2002, 13 (05) : 486 - 492
  • [33] Improved synthesis of the enantiomers of propafenone using chiral building blocks
    Ecker, G
    Noe, CR
    Fleischhacker, W
    MONATSHEFTE FUR CHEMIE, 1997, 128 (01): : 53 - 59
  • [34] Simultaneous Process Synthesis and Process Intensification using Building Blocks
    Li, Jianping
    Demirel, Salih Emre
    Hasan, M. M. Faruque
    27TH EUROPEAN SYMPOSIUM ON COMPUTER AIDED PROCESS ENGINEERING, PT A, 2017, 40A : 1171 - 1176
  • [35] A working model of protein synthesis using Lego™ building blocks
    Templin, MA
    Fetters, MK
    AMERICAN BIOLOGY TEACHER, 2002, 64 (09): : 673 - 678
  • [36] Efficient synthesis of phosphotyrosine building blocks using imidazolium trifluoroacetate
    Gomez, Cindy
    Chen, Jianyong
    Wang, Shaomeng
    TETRAHEDRON LETTERS, 2009, 50 (48) : 6691 - 6692
  • [37] Improved Synthesis of the Enantiomers of Propafenone Using Chiral Building Blocks
    Ecker, G.
    Noe, C. R.
    Fleischhacker, W.
    Monatshefte fuer Chemie, 128 (01):
  • [38] The synthesis and curing kinetics study of a new fluorinated polyurethane with fluorinated side chains attached to soft blocks
    Li, Lingling
    Wang, Xia
    Li, Zan
    Bi, Wei
    Li, Ying
    Qi, Yuanchun
    Dong, Qingzhi
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (01) : 596 - 605
  • [39] Chemoenzymatic synthesis of statine side chain building blocks and application in the total synthesis of the cholesterol-lowering compound
    Rieder, Oliver
    Wolberg, Michael
    Foegen, Silke E.
    Mueller, Michael
    JOURNAL OF BIOTECHNOLOGY, 2017, 258 : 171 - 180
  • [40] Side reactions in solid phase peptide synthesis caused by sulfonyl-ornithine building blocks
    Link, A
    Lescrinier, T
    Kerremans, L
    Rozenski, J
    Herdewijn, P
    PHARMAZIE, 1998, 53 (03): : 200 - 201