Construction of key building blocks towards the synthesis of cortistatins

被引:5
|
作者
Indu, Satrajit [1 ]
Telore, Rahul D. [1 ]
Kaliappan, Krishna P. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
关键词
FORMAL TOTAL-SYNTHESIS; ENYNE METATHESIS APPROACH; STEROIDAL ALKALOIDS; CONCISE SYNTHESIS; SCALABLE SYNTHESIS; CORE STRUCTURE; RING STRUCTURE; B-RING; ANGIOGENESIS; PROTECTION;
D O I
10.1039/d0ob00170h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work reports the construction of key building blocks towards the synthesis of cortistatins; a family of steroidal alkaloids. Cortistatin A, being a primary target due to its superior biological properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from d-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A.
引用
收藏
页码:2432 / 2446
页数:15
相关论文
共 50 条
  • [21] Synthesis of aromatic glycoconjugates. Building blocks for the construction of combinatorial glycopeptide libraries
    Noerrlinger, Markus
    Ziegler, Thomas
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 2453 - 2460
  • [22] Total Synthesis of Cortistatins A and J
    Yamashita, Shuji
    Iso, Kentaro
    Kitajima, Kazuki
    Himuro, Masafumi
    Hirama, Masahiro
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08): : 2408 - 2425
  • [23] Synthesis of new building blocks: Towards the analogs of peptide nucleic acids (PNAs)
    Dallaire, C
    Arya, P
    TETRAHEDRON LETTERS, 1998, 39 (29) : 5129 - 5132
  • [24] TOTAL SYNTHESIS OF AMPHOTERONOLIDE-B AND AMPHOTERICIN-B .1. STRATEGY AND STEREOCONTROLLED CONSTRUCTION OF KEY BUILDING-BLOCKS
    NICOLAOU, KC
    DAINES, RA
    UENISHI, J
    LI, WS
    PAPAHATJIS, DP
    CHAKRABORTY, TK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) : 4672 - 4685
  • [25] Studies towards the total synthesis of mumbaistatin: synthesis of highly substituted benzophenone and anthraquinone building blocks
    Kaiser, F
    Schwink, L
    Velder, J
    Schmalz, HG
    TETRAHEDRON, 2003, 59 (18) : 3201 - 3217
  • [26] A simple access to key pyridine building blocks
    Cabanal-Duvillard, I
    Berrien, JF
    HETEROCYCLIC COMMUNICATIONS, 1999, 5 (03) : 257 - 262
  • [27] Synthesis of fluorinated building blocks
    Forgey, Rashel
    Easdon, Jerry C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [28] Synthesis of cortistatins A, J, K and L
    Alec N. Flyer
    Chong Si
    Andrew G. Myers
    Nature Chemistry, 2010, 2 : 886 - 892
  • [29] Metal-Free Synthesis of Polysubstituted Triazoloquinoxalines Using Alkynols as the Key Building Blocks
    Masaryk, Berenika
    Soural, Miroslav
    ACS OMEGA, 2024, 9 (37): : 38569 - 38582
  • [30] Synthesis of ortho-perfluoroalkyl phenones from hemifluorinated enones as key building blocks
    Chanteau, Frederic
    Plantier-Royon, Richard
    Haufe, Guenter
    Portella, Charles
    TETRAHEDRON, 2006, 62 (38) : 9049 - 9053