Total Synthesis and Determination of the Absolute Configuration of Vinylamycin

被引:15
作者
Yang, Zhantao [1 ,2 ]
Yang, Guang [1 ,2 ]
Ma, Meiyan [1 ,2 ]
Li, Jiangnan [3 ]
Liu, Jianwei [1 ,2 ]
Wang, Jinghan [1 ,2 ]
Jiang, Shende [3 ]
Zhang, Quan [1 ,2 ]
Chen, Yue [1 ,2 ]
机构
[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Coll Pharm, State Key Lab Med Chem Biol, Tianjin 300071, Peoples R China
[2] Nankai Univ, Tianjin Key Lab Mol Drug Res, Tianjin 300071, Peoples R China
[3] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
RAKICIDIN;
D O I
10.1021/acs.orglett.5b02809
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute configurations of the three unknown chiral centers in vinylamycin were predicted according to the structural comparison with microtermolide A and rakicidin A, and then total syntheses of vinylamycin were applied to determine the three unknown chiral centers as 14R, 15R, and 16S.
引用
收藏
页码:5725 / 5727
页数:3
相关论文
共 18 条
  • [1] Microtermolides A and B from Termite-Associated Streptomyces sp and Structural Revision of Vinylamycin
    Carr, Gavin
    Poulsen, Michael
    Klassen, Jonathan L.
    Hou, Yanpeng
    Wyche, Thomas P.
    Bugni, Tim S.
    Currie, Cameron R.
    Clardy, Jon
    [J]. ORGANIC LETTERS, 2012, 14 (11) : 2822 - 2825
  • [2] Stereoselective synthesis of MeBmt and methyl (4R,5S)-5-isopropyl-2-phenyloxazoline-4-carboxylate by a Pd-catalyzed equilibration
    Cook, GR
    Shanker, PS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) : 6818 - 6822
  • [3] Hu JF, 2000, EUR J ORG CHEM, V2000, P3353
  • [4] Vinylamycin, a new depsipeptide antibiotic, from Streptomyces sp.
    Igarashi, M
    Shida, T
    Sasaki, Y
    Kinoshita, N
    Naganawa, H
    Hamada, M
    Takeuchi, T
    [J]. JOURNAL OF ANTIBIOTICS, 1999, 52 (10) : 873 - 879
  • [5] Rakicidin D, an inhibitor of tumor cell invasion from marine-derived Streptomyces sp.
    Igarashi, Yasuhiro
    Shimasaki, Ryoko
    Miyanaga, Satoshi
    Oku, Naoya
    Onaka, Hiroyasu
    Sakurai, Hiroaki
    Saiki, Ikuo
    Kitani, Shigeru
    Nihira, Takuya
    Wimonsiravude, Waurawan
    Panbangred, Watanalai
    [J]. JOURNAL OF ANTIBIOTICS, 2010, 63 (09) : 563 - 565
  • [6] Total synthesis of stevastelins: Structure confirmation of stevastelins B and B3, and structure revision of stevastelin C3
    Kurosawa, Kazuo
    Matsuura, Keigo
    Nagase, Toshihiko
    Chida, Noritaka
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2006, 79 (06) : 921 - 937
  • [7] Rakicidins, new cytotoxic lipopeptides from Micromonospora sp Fermentation, isolation and characterization
    McBrien, KD
    Berry, RL
    Lowe, SE
    Neddermann, KM
    Bursuker, I
    Huang, S
    Klohr, SE
    Leet, JE
    [J]. JOURNAL OF ANTIBIOTICS, 1995, 48 (12) : 1446 - 1452
  • [8] Nishioka H., 1998, [No title captured], Patent No. [JP10147594-A, 10147594, JP 10147594 A]
  • [9] Induced production of emericellamides A and B from the marine-derived fungus Emericella sp in competing co-culture
    Oh, Dong-Chan
    Kauffman, Christopher A.
    Jensen, Paul R.
    Fenical, William
    [J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (04): : 515 - 520
  • [10] Complete Stereochemistry and Preliminary Structure-Activity Relationship of Rakicidin A, a Hypoxia-Selective Cytotoxin from Micromonospora sp.
    Oku, Naoya
    Matoba, Shouhei
    Yamazaki, Yohko Momose
    Shimasaki, Ryoko
    Miyanaga, Satoshi
    Igarashi, Yasuhiro
    [J]. JOURNAL OF NATURAL PRODUCTS, 2014, 77 (11): : 2561 - 2565