Total Synthesis of Azumamide E and Sugar Amino Acid-Containing Analogue

被引:32
作者
Chandrasekhar, Srivari [1 ]
Rao, Chennamaneni Lohitha [1 ]
Seenaiah, Mallikanti [1 ]
Naresh, Police [2 ]
Jagadeesh, Bharatam [2 ]
Manjeera, Dharani [3 ]
Sarkar, Arpita [3 ]
Bhadra, Manika Pal [3 ]
机构
[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500607, Andhra Pradesh, India
[2] Indian Inst Chem Technol, Ctr Nucl Magnet Resonance, Hyderabad 500607, Andhra Pradesh, India
[3] Indian Inst Chem Technol, Ctr Chem Biol, Hyderabad 500607, Andhra Pradesh, India
关键词
HISTONE DEACETYLASE INHIBITORS; CYCLIC TETRAPEPTIDES; DERIVATIVES;
D O I
10.1021/jo8020264
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and practical total synthesis of marine cyclic tetrapeptide. natural product azumamide E (1) is achieved via hi-h-yielding reactions. The strategy also allowed us to synthesize the azumamide E-SAA (sugar amino acid) analogue (2), whose solution-phase NMR and biological activity studies were also carried out.
引用
收藏
页码:401 / 404
页数:4
相关论文
共 27 条
  • [1] Expanding the conformational pool of cis-β-sugar amino acid:: Accommodation of β-hGly motif in robust 14-helix
    Chandrasekhar, S
    Reddy, MS
    Babu, BN
    Jagadeesh, B
    Prabhakar, A
    Jagannadh, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (27) : 9664 - 9665
  • [2] Formation of a stable 14-helix in short oligomers of furanoid cis-β-sugar-amino acid'
    Chandrasekhar, S
    Reddy, MS
    Jagadeesh, B
    Prabhakar, A
    Rao, MHVR
    Jagannadh, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) : 13586 - 13587
  • [3] ENANTIOSELECTIVE SYNTHESIS OF SITOPHILATE, THE GRANARY WEEVIL AGGREGATION PHEROMONE
    CHONG, JM
    [J]. TETRAHEDRON, 1989, 45 (03) : 623 - 628
  • [4] EITER K, 1978, LIEBIGS ANN CHEM, P658
  • [5] Facile preparation of nucleoside-5′-carboxylic acids
    Epp, JB
    Widlanski, TS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) : 293 - 295
  • [6] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
    GAO, Y
    HANSON, RM
    KLUNDER, JM
    KO, SY
    MASAMUNE, H
    SHARPLESS, KB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
  • [7] GEORGE AY, 2004, J AM CHEM SOC, V126, P1030
  • [8] Improved total synthesis of the potent HDAC inhibitor FK228 (FR-901228)
    Greshock, Thomas J.
    Johns, Deidre M.
    Noguchi, Yasuo
    Williams, Robert M.
    [J]. ORGANIC LETTERS, 2008, 10 (04) : 613 - 616
  • [9] Sugar amino acid containing somatostatin analogues that induce apoptosis in both drug-sensitive and multidrug-resistant tumor cells
    Gruner, SAW
    Kéri, G
    Schwab, R
    Venetianer, A
    Kessler, H
    [J]. ORGANIC LETTERS, 2001, 3 (23) : 3723 - 3725
  • [10] Total synthesis of azumamides A and E
    Izzo, Irene
    Maulucci, Nakia
    Bifulco, Giuseppe
    De Riccardis, Francesco
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) : 7557 - 7560