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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 50期
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
  • [31] Protecting-group-free glycosylation of phosphatidic acid in aqueous media
    Kano, Koki
    Ishii, Nozomi
    Miyagawa, Atsushi
    Takeda, Hiroaki
    Hirabayashi, Yoshio
    Kamiguchi, Hiroyuki
    Greimel, Peter
    Matsuo, Ichiro
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (10) : 2138 - 2142
  • [32] Protecting-group-free amination of halogenated nitrobenzaldehyde with palladium catalyst
    Cao, Jing
    Feng, Jun Xiang
    Wu, Yong Xiang
    Tuo, Ya Ya
    CHINESE CHEMICAL LETTERS, 2010, 21 (08) : 935 - 938
  • [33] Concise Total Synthesis of Dioncophylline E through an ortho-Arylation Strategy
    Toop, Hamish D.
    Brusnahan, Jason S.
    Morris, Jonathan C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (29) : 8536 - 8538
  • [34] Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products
    Wang, Hong-Shuang
    Li, Hui-Jing
    Wang, Jun-Li
    Wu, Yan-Chao
    GREEN CHEMISTRY, 2017, 19 (09) : 2140 - 2144
  • [35] Protecting-Group-Free Synthesis of Amines: Synthesis of Primary Amines from Aldehydes via Reductive Amination
    Dangerfield, Emma M.
    Plunkett, Catherine H.
    Win-Mason, Anna L.
    Stocker, Bridget L.
    Timmer, Mattie S. M.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16) : 5470 - 5477
  • [36] Protecting-Group-Free Synthesis of Novel Cannabinoid-Like 2,5-Dihydrobenzoxepines
    Nguyen, Gia-Nam
    Jordan, Erin Noel
    Kayser, Oliver
    SYNTHESIS-STUTTGART, 2022, 54 (24): : 5540 - 5550
  • [37] Concise Total Synthesis of Ivorenolide B
    Ungeheuer, Felix
    Fuerstner, Alois
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) : 11387 - 11392
  • [38] Protecting-Group-Free Total Synthesis of Isoquinoline Alkaloids by Nickel-Catalyzed Annulation of o-Halobenzaidimine with an Alkyne as the Key Step
    Korivi, Rajendra Prasad
    Cheng, Chien-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) : 282 - 287
  • [39] The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D
    Gordon, Jonny R.
    Nelson, Hosea M.
    Virgil, Scott C.
    Stoltz, Brian M.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) : 9740 - 9747
  • [40] A concise and straightforward approach to total synthesis of (+)-Strictifolione and formal synthesis of Cryptofolione via a unified strategy
    Li, Xiaotong
    Wang, Gaopeng
    Zhang, Zhibin
    Wu, Na
    Yang, Qianqian
    Huang, Shuangping
    Wang, Xiaoji
    SYNTHETIC COMMUNICATIONS, 2019, 49 (08) : 1031 - 1039
12345