Total synthesis of siomycin A

被引:19
作者
Mori, Tomonori [1 ]
Higashibayashi, Shuhei [1 ]
Goto, Taiji [1 ]
Kohno, Mitsunori [1 ]
Satouchi, Yukiko [1 ]
Shinko, Kazuyuki [1 ]
Suzuki, Kengo [1 ]
Suzuki, Shunya [1 ]
Tohmiya, Hiraku [1 ]
Hashimoto, Kimiko [1 ]
Nakata, Masaya [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
siomycin A; one-pot cyclization-elongation; thiazoline; dehydroamino acid;
D O I
10.1016/j.tetlet.2006.12.121
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have succeeded in the total synthesis of siomycin A, a representative compound of the thiostrepton family of peptide antibiotics, featuring the one-pot cyclization-elongation of our strategic intermediates and the late-stage formations of the thiazoline and dehydroamino acid moieties. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1331 / 1335
页数:5
相关论文
共 50 条
[1]   Total synthesis of siomycin A: Completion of the total synthesis [J].
Mori, Tomonori ;
Higashibayashi, Shuhei ;
Goto, Taiji ;
Kohno, Mitsunori ;
Satouchi, Yukiko ;
Shinko, Kazuyuki ;
Suzuki, Kengo ;
Suzuki, Shunya ;
Tohmiya, Hiraku ;
Hashimoto, Kimiko ;
Nakata, Masaya .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (06) :1013-1025
[2]   Total synthesis of siomycin A: Construction of synthetic segments [J].
Mori, Tomonori ;
Higashibayashi, Shuhei ;
Goto, Taiji ;
Kohno, Mitsunori ;
Satouchi, Yukiko ;
Shinko, Kazuyuki ;
Suzuki, Kengo ;
Suzuki, Shunya ;
Tohmiya, Hiraku ;
Hashimoto, Kimiko ;
Nakata, Masaya .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (06) :984-1012
[3]   Effects and mechanism of siomycin A on the growth and apoptosis of MiaPaCa-2 cancer cells [J].
Wang, Bin ;
Wang, Wei ;
Meng, Hao-Yi ;
Chen, Jing ;
Yuan, Li-Jie .
ONCOLOGY LETTERS, 2019, 18 (03) :2869-2876
[4]   Total synthesis of (-)-tantazole B [J].
Parsons, RL ;
Heathcock, CH .
SYNLETT, 1996, (12) :1168-&
[5]   Total synthesis of largamide H [J].
Liang, Shuo ;
Xu, Zhengshuang ;
Ye, Tao .
CHEMICAL COMMUNICATIONS, 2010, 46 (01) :153-155
[6]   Total synthesis of didmolamides A and B [J].
You, SL ;
Kelly, JW .
TETRAHEDRON LETTERS, 2005, 46 (15) :2567-2570
[7]   Siomycin A induces reactive oxygen species-mediated cytotoxicity in ovarian cancer cells [J].
Shao, Xiulan ;
Zhang, Fengying ;
Gao, Xiang ;
Xu, Fengying .
ONCOLOGY LETTERS, 2021, 21 (06)
[8]   Total synthesis of telomestatin and its analogues [J].
Doi, Takayuki ;
Yoshida, Masahito ;
Shibata, Kazuaki .
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2015, 73 (01) :3-13
[9]   Total synthesis involving sulfur chemistry [J].
Fukuyama, Tohru .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (07) :630-633
[10]   Total Synthesis and Biological Evaluation of Grassypeptolide A [J].
Liu, Hui ;
Liu, Yuqing ;
Wang, Zhuo ;
Xing, Xiangyou ;
Maguire, Anita R. ;
Luesch, Hendrik ;
Zhang, Hui ;
Xu, Zhengshuang ;
Ye, Tao .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (21) :6774-6784