Concise Total Synthesis of Sintokamides A, B, and E by a Unified, Protecting-Group-Free Strategy

被引:86
|
作者
Gu, Zhenhua [1 ]
Zakarian, Armen [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
基金
美国国家卫生研究院;
关键词
chlorine; natural products; peptides; total synthesis; trichloromethylation; MARINE NATURAL-PRODUCTS; KETENE SILYL ACETALS; TETRAMIC ACIDS; BARBAMIDE BIOSYNTHESIS; PEPTIDE-SYNTHESIS; DYSIDEA SP; ANALOGS; HALOGENATION; REBECCAMYCIN; DERIVATIVES;
D O I
10.1002/anie.201005354
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
One for all: A group of polychlorinated marine peptides known as sintokamides show intriguing activity against hormone-refractory prostate cancer cells. Three members of the group have now been synthesized by a general strategy enabled by a ruthenium-catalyzed radical chloroalkylation of titanium enolates (see scheme). Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9702 / 9705
页数:4
相关论文
共 50 条
  • [1] Scalable Total Synthesis of (-)-Berkelic Acid by Using a Protecting-Group-Free Strategy
    Fananas, Francisco J.
    Mendoza, Abraham
    Arto, Tamara
    Temelli, Baris
    Rodriguez, Felix
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (20) : 4930 - 4933
  • [2] Asymmetric, Protecting-Group-Free Total Synthesis of (+)-Caribenol A
    Han, Jing-Chun
    Liu, Lian-Zhu
    Li, Chuang-Chuang
    Yang, Zhen
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (09) : 1972 - 1975
  • [3] Protecting-Group-Free Total Synthesis of 8-Methoxygoniodiol
    Ramesh, Perla
    SYNTHESIS-STUTTGART, 2016, 48 (23): : 4300 - 4304
  • [4] Protecting-Group-Free Total Synthesis of (-)-Pallambins A-D
    Zhang, Xiwu
    Wang, Yuan
    Chen, Peng
    Cai, Xinxian
    Jia, Yanxing
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (07) : 1983 - 1996
  • [5] Asymmetric, Protecting-Group-Free Total Synthesis of (-)-Englerin A
    Zhou, Qianghui
    Chen, Xiaofei
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (20) : 3513 - 3516
  • [6] Protecting-Group-Free Total Synthesis and Biological Investigation of Cabucine Oxindole A†
    Xie, Shengling
    Ning, Chengqing
    Yu, Qingzhen
    Hou, Jieping
    Xu, Jing
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (01): : 137 - 142
  • [7] Protecting-group-free total synthesis of 4-epi-phomonol
    Wang, Xiang
    Feng, Ruokun
    Qi, Chenze
    Yang, Zhen
    TETRAHEDRON LETTERS, 2017, 58 (37) : 3588 - 3589
  • [8] Divergent Synthetic Route to Oxidized Benzofulvene Sesquiterpenoids: Protecting-Group-Free Total Synthesis of Nicotianasesterpenes A, B, and a Polygonum Sesquiterpenoid
    Jeong, Myeonggyo
    Lee, Hyunkee
    Kim, Gibeom
    Jo, Jeyun
    Chang, Jae Won
    Jung, Jee H.
    Suh, Young-Ger
    Yun, Hwayoung
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (39) : 6714 - 6719
  • [9] Protecting-group-free catalytic asymmetric total synthesis of (-)-rosmarinecine
    Nemoto, Hiroyuki
    Tanimoto, Kouichi
    Kanao, Yukiko
    Omura, Sohei
    Kita, Yasuyuki
    Akai, Shuji
    TETRAHEDRON, 2012, 68 (36) : 7295 - 7301
  • [10] Protecting-group-free formal synthesis of platensimycin
    Tiefenbacher, Konrad
    Mulzer, Johann
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) : 8074 - 8075