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 49 条
  • [1] USE OF ESTERS OF N-HYDROXYSUCCINIMIDE IN PEPTIDE SYNTHESIS
    ANDERSON, GW
    CALLAHAN, FM
    ZIMMERMAN, JE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (09) : 1839 - +
  • [2] [Anonymous], 2007, WAY SYNTHESIS EVOLUT
  • [3] NMR J-based analysis of nitrogen-containing moieties and application to dysithiazolamide, a new polychlorinated dipeptide from Dysidea sp.
    Ardá, A
    Rodríguez, J
    Nieto, RM
    Bassarello, C
    Gomez-Paloma, L
    Bifulco, G
    Jiménez, C
    [J]. TETRAHEDRON, 2005, 61 (42) : 10093 - 10098
  • [4] Total synthesis of (-)-dysithiazolamide
    Arda, Ana
    Soengas, Raquel G.
    Nieto, M. Isabel
    Jimenez, Carlos
    Rodriguez, Jaime
    [J]. ORGANIC LETTERS, 2008, 10 (11) : 2175 - 2178
  • [5] REGIOSPECIFIC O-ALKYLATION OF BETA-TETRONIC ACIDS UNDER MITSUNOBU REACTION CONDITIONS
    BAJWA, JS
    ANDERSON, RC
    [J]. TETRAHEDRON LETTERS, 1990, 31 (48) : 6973 - 6976
  • [6] Total synthesis of marine natural products without using protecting groups
    Baran, Phil S.
    Maimone, Thomas J.
    Richter, Jeremy M.
    [J]. NATURE, 2007, 446 (7134) : 404 - 408
  • [7] Valence Tautomerism in Titanium Enolates: Catalytic Radical Haloalkylation and Application in the Total Synthesis of Neodysidenin
    Beaumont, Stephane
    Ilardi, Elizabeth A.
    Monroe, Lucas R.
    Zakarian, Armen
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1482 - +
  • [8] Synthetic studies of trichloroleucine marine natural products.: Michael addition of LiCCl3 to N-crotonylcamphor sultam
    Brantley, SE
    Molinski, TF
    [J]. ORGANIC LETTERS, 1999, 1 (13) : 2165 - 2167
  • [9] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE
    CARPINO, LA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4397 - 4398
  • [10] Dichlorination of a pyrrolyl-S-carrier protein by FADH2-dependent halogenase PltA during pyoluteorin biosynthesis
    Dorrestein, PC
    Yeh, E
    Garneau-Tsodikova, S
    Kelleher, NL
    Walsh, CT
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (39) : 13843 - 13848