Total Synthesis and Biological Evaluation of the Tetramic Acid Based Natural Product Harzianic Acid and Its Stereoisomers

被引：26
|
作者：
Healy, Alan R. [1 ,2 ]
Vinale, Francesco [3 ]
Lorito, Matteo [3 ,4 ]
Westwood, Nicholas J. [1 ,2 ]
机构：
[1] Univ St Andrews, Sch Chem & Biomed Sci Res Complex, St Andrews KY16 9ST, Fife, Scotland
[2] EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[3] CNR, IPSP, I-80055 Portici, Italy
[4] Univ Napoli Federico II, Dipartimento Agr, I-80138 Portici, Italy
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 03期
关键词：
TRICHODERMA; INHIBITOR;
D O I：
10.1021/ol503717r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.
引用
收藏
页码：692 / 695
页数：4
相关论文
共 50 条
  • [41] SYNTHESIS AND BIOLOGICAL EVALUATION OF ISOFOLIC ACID
    NAIR, MG
    BAUGH, CM
    JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (02) : 223 - 226
  • [42] Synthesis and biological evaluation of calcioic acid
    Yu, Olivia B.
    Mutchie, Tania R.
    Di Milo, Elliot S.
    Arnold, Leggy A.
    STEROIDS, 2020, 154
  • [43] Piperazic acid-containing natural products: Isolation, biological relevance and total synthesis
    Oelke, Alexander J.
    France, David J.
    Hofmann, Tatjana
    Wuitschik, Georg
    Ley, Steven V.
    NATURAL PRODUCT REPORTS, 2011, 28 (08) : 1445 - 1471
  • [44] Total Synthesis of Largazole and Its Biological Evaluation
    Numajiri, Yoshitaka
    Takahashi, Takashi
    Takagi, Motoki
    Shin-ya, Kazuo
    Doi, Takayuk
    SYNLETT, 2008, (16) : 2483 - 2486
  • [45] Asymmetric total synthesis of (+)-carneic acid A and structure revision of its natural form
    Yamakoshi, Shuhei
    Hayashi, Nobuyuki
    Suzuki, Takahiro
    Nakada, Masahisa
    TETRAHEDRON LETTERS, 2009, 50 (38) : 5372 - 5375
  • [46] Total synthesis and biological evaluation of peptide natural products
    Inoue, Masayuki
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [47] Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins
    Nicolaou, K. C.
    Yun, Jun
    Mandal, Debashis
    Erande, Rohan D.
    Klahn, Philipp
    Jin, Michael
    Aujay, Monette
    Sandoval, Joseph
    Gavrilyuk, Julia
    Vourloumis, Dionisios
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (05) : 1698 - 1708
  • [48] SYNTHESIS, RESOLUTION, AND BIOLOGICAL EVALUATION OF THE 4 STEREOISOMERS OF 4-METHYLGLUTAMIC ACID - SELECTIVE PROBES OF KAINATE RECEPTORS
    GU, ZQ
    HESSON, DP
    PELLETIER, JC
    MACCECCHINI, ML
    ZHOU, LM
    SKOLNICK, P
    JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) : 2518 - 2520
  • [49] Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers
    Zhang, Yang-Ming
    Ding, Yu
    Tang, Wei
    Luo, Wei
    Gu, Min
    Lu, Wei
    Tang, Jie
    Zuo, Jian-Ping
    Nan, Fa-Jun
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (20) : 9212 - 9216
  • [50] Toward the total synthesis of pseudolaric acid B. Preparation of a key intermediate by degradation and its use in the reassembly of the natural product
    Wu, BG
    Karle, JM
    Watkins, EB
    Avery, MA
    TETRAHEDRON LETTERS, 2002, 43 (22) : 4095 - 4098
12345