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
  • [21] Synthesis and Wetting Behavior of Polyurethanes Containing Polyoxetane Soft Blocks with Semifluorinated and Bromomethyl Side Chains
    黄继庆
    王君
    孟卫东
    卿凤翎
    Journal of Donghua University(English Edition), 2010, 27 (05) : 593 - 599
  • [22] Synthesis and wetting behavior of polyurethanes containing polyoxetane soft blocks with semifluorinated and bromomethyl side chains
    Huang, Ji-Qing
    Wang, Jun
    Meng, Wei-Dong
    Qing, Feng-Ling
    Journal of Donghua University (English Edition), 2010, 27 (05) : 593 - 599
  • [23] 1,2,3-THIADIAZOLES WITH UNSATURATED SIDE-CHAINS MONOMERIC BUILDING-BLOCKS FOR PHOTORESISTS
    HANOLD, N
    KALBITZ, H
    ALSMADI, M
    MEIER, H
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1995, 50 (07): : 1121 - 1126
  • [24] Synthesis of poly(β-amino ester)s with thiol-reactive side chains for DNA delivery
    Zugates, Gregory T.
    Anderson, Daniel G.
    Little, Steven R.
    Lawhorn, Ingrid E. B.
    Langer, Robert
    Journal of the American Chemical Society, 2006, 128 (39): : 12726 - 12734
  • [25] Synthesis and Properties of α-1,3-Glucan with Branched and Linear Mixed Ester Side Chains
    Fukata, Yuya
    Kimura, Satoshi
    Iwata, Tadahisa
    ACS APPLIED POLYMER MATERIALS, 2021, 3 (01): : 418 - 425
  • [26] Synthesis and Helical Structure of Poly(1-methylpropargyl ester)s with Various Side Chains
    Suzuki, Yuji
    Shiotsuki, Masashi
    Sanda, Fumio
    Masuda, Toshio
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (12) : 2075 - 2081
  • [27] Synthesis of poly(β-amino ester)s with thiol-reactive side chains for DNA delivery
    Zugates, Gregory T.
    Anderson, Daniel G.
    Little, Steven R.
    Lawhorn, Ingrid E. B.
    Langer, Robert
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12726 - 12734
  • [28] Synthesis of the ester side chains of some potently antileukemic harringtonia alkaloids from chiral citrates
    Ancliff, Rachael A.
    Russell, Andrew T.
    Sanderson, Adam J.
    CHEMICAL COMMUNICATIONS, 2006, (30) : 3243 - 3245
  • [29] SYNTHESIS OF USEFUL BUILDING BLOCKS FOR PEPTIDE SYNTHESIS: A COMPARATIVE STUDY OF DIFFERENT COUPLING REAGENTS FOR ESTER AND AMIDE BONDS
    Pozo-Carrero, M. C.
    Kolesinska, B.
    Sabatino, G.
    Chelli, M.
    Rovero, P.
    Kaminski, Z. J.
    Papini, A. M.
    JOURNAL OF PEPTIDE SCIENCE, 2004, 10 : 133 - 133
  • [30] Novel ester linked glycosyl amino acids: convenient building blocks for the synthesis of glycopeptide libraries
    Tennant-Eyles, RJ
    Fairbanks, AJ
    TETRAHEDRON-ASYMMETRY, 1999, 10 (02) : 391 - 401