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

页码：9702 / 9705

页数：4

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

← 1 2 3 4 5 →