A general method for the synthesis of bastaranes and isobastaranes: First total synthesis of bastadins 5, 10, 12, 16, 20, and 21

Couladouros EA; Pitsinos EN; Moutsos VI; Sarakinos G

首页> 外文期刊>Chemistry: A European journal >A general method for the synthesis of bastaranes and isobastaranes: First total synthesis of bastadins 5, 10, 12, 16, 20, and 21

【24h】

A general method for the synthesis of bastaranes and isobastaranes: First total synthesis of bastadins 5, 10, 12, 16, 20, and 21

机译：合成Bastaranes和isobastaranes的一般方法：第一个总合成巴斯塔锡5,10,12,16,20和21

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

A general strategy for the synthesis of twenty naturally occurring bastadins (all but bastadin 3) is presented. A key retrosynthetic disconnection of the two amide bonds, common in all target molecules, bisects the macrocyclic core into two diaryl ether fragments, an alpha,omega-diamine (western part) and an alpha,omega-dicarboxylic acid (eastern part). Efficient preparation of the synthetically challenging o-mono or dibromo-substituted diaryl ether linkages was achieved employing the diaryl iodonium salt method. Regarding the western part, variations of the aliphatic chain were more efficiently secured by the preparation of two different alpha,omega-aminonitrile moieties. Cobalt boride mediated reduction of the nitrile functionality established the required diamines and, at the same time, provided the necessary variation of the aromatic-ring bromination pattern. Regarding the eastern part, two different dicarboxyl precursors had to be prepared in order to accommodate bromination-pattern variations. Coupling and subsequent macrolactamization of different combinations of these key intermediates may lead at will to any member of this family of marine natural products. Four bastaranes (bastadins 5, 10, 12 and 16) and two isobastaranes (bastadins 20 and 21) were synthesized as a demonstration of the flexibility and efficiency of the approach presented.

机译：介绍了合成20天然存在的副杀蛋白的一般策略（All但Bastadin 3）。两个酰胺键的关键逆转性断开在所有靶分子中常见，使大环核分为两种二芳基醚片段，α，ω-二胺（西部）和α，ω二羧酸（东部）。使用二芳基碘鎓盐法实现了合成挑战的O-Mono或二溴取代的二芳基醚键的高效制备。关于西部，通过制备两种不同的α，甘露腈部分，更有效地确保了脂族链的变化。硼化钴介导的丁腈官能度的降低建立了所需的二胺，同时提供芳香环溴化图案的必要变化。关于东部，必须制备两种不同的二羧基前体，以适应溴化溴化型变化。这些关键中间体的不同组合的偶联和随后的Macroactamization可能会导致该家庭海洋天然产物的任何成员的意志。合成了四种混蛋（巴斯塔丁酸盐5,10,12和16）和两种含有屠杀20和21），作为呈现的灵活性和效率的证明。

著录项

来源
《Chemistry: A European journal》 |2004年第1期|共16页
作者
Couladouros EA; Pitsinos EN; Moutsos VI; Sarakinos G;
展开▼
作者单位

Agr Univ Athens Chem Labs GR-11855 Athens Greece;

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类化学;
关键词
diaryl ethers; hypervalent compounds; natural products; oximino amides; total synthesis; SPONGE IANTHELLA-BASTA; TYROSINE-DERIVED METABOLITES; MARINE SPONGE; ASYMMETRIC DIHYDROXYLATION; CODONOCARPUS ALKALOIDS; N-BROMOSUCCINIMIDE; SKELETAL-MUSCLE; DIARYL ETHERS; RECEPTOR; PHENOLS;

机译：杂志;天然产品;奥昔诺酰胺;总合成;海绵Ianthella-Basta;酪氨酸衍生的代谢物;海绵;不对称二羟基化;Codonocarpus生物碱;N-溴嘧啶;骨骼肌肉;骨肌;受体;受体;苯酚;

相似文献

外文文献
中文文献
专利

1. A General Method for the Synthesis of Bastaranes and Isobastaranes:First Total Synthesis of Bastadins 5,10,12,16,20,and 21 [J] . Elias A.Couladouros, Emmanuel N.Pitsinos, Vassilios I.Moutsos, Chemistry: A European journal . 2005,第1期

机译：合成Bastaranes和Isobastaranes的通用方法：Bastadins 5、10、12、16、20和21的首次全合成
2. Synthesis, characterization and antimicrobial activities of homo- and bimetallic trinuclear complexes of a 30-membered macrocyclic ligand [30] 1,4,5,9,10,13, 16,19,20,24,25,28-dodecaaza-2,3,11,12,17,18,26,27-octaphenyl-6,8,21,23-tetramethylcyclotriaconta-1,3,5,8,10,12,16,18,20,23,25,27-dodecaene (L) [J] . S. K. Tripathy, A. Panda, P. K. Das Journal of the Indian Chemical Society . 2014,第7期

机译：30元大环配体的同金属和双金属三核配合物的合成，表征和抗菌活性[30] 1,4,5,9,10,13,16,19,20,24,25,28-dodecaaza-2 ，3,11,12,17,18,26,27-八苯基-6,8,21,23-四甲基环三a-1,3,5,8,10,12,16,18,20,23,25,27 -十二碳烯（L）
3. Stereochemical Definition of the Natural Product (6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)-Azaspiracid-3 by Total Synthesis and Comparative Analyses [J] . Kenton Nathaniel T., Adu-Ampratwum Daniel, Okumu Antony A., Angewandte Chemie . 2018,第3期

机译：天然产品的立体化学定义（6R，10R，13R，14R，16R，17R，19S，20S，21R，24S，25S，28S，30S，32R，33R，34R，36S，37S，39R）-Azaspiracid-3 总合成和比较分析
4. THEORETICAL INVESTIGATION OF A HIGH ENERGETIC 2,4,6,8,11,13,15,17,19,22,23,24-DODECANITRO-2,4,6,8,11,13,15,17,19,22,23,24-DODECAAZA-NONACYCLO16.4.1~(9,21).1~(10,20).0~(1,9).0~(3,7).0~(3,16).0~(5,14).0~(7,12).0~(10,18).0~(12,16) TETRACOSANE [C] . Guozheng Zhao, Ming Lu International annual conference of Fraunhofer ITC . 2014

机译：2,4,6,8,11,13,15,17,19,22,23,24-DODECANITRO-2,4,6,8,11,13,15,17,19，的高能理论研究22,23,24-DODECAAZA-NONACYCLO 16.4.1〜（9,21）.1〜（10,20）.0〜（1,9）.0〜（3,7）.0〜（3,16 ）.0〜（5,14）.0〜（7,12）.0〜（10,18）.0〜（12,16）四碳烷
5. Mixture synthesis of a 16-member murisolin stereoisomer library & synthesis of C1-C20 and C21-C40 fragments of tetrafibricin. [D] . Gudipati, Venugopal. 2008

机译：16元murisolin立体异构体库的混合物合成和四纤蛋白的C1-C20和C21-C40片段的合成。
6. Synthesis crystal structure and characterizations of di-μ-cyanido-1:2κ2N:C;2:3κ2C:N-bis(4713162124-hexaoxa-110-diazabicyclo8.8.8hexacosane)-1κ8N1N10O4O7O13O16O21O24;3κ8N1N10O4O7O13O16O21O24-5101520-tetrakis(4-chlorophenyl)porphyrinato-2κ4N-2-iron(II)-13-dipotassium(I) tetrahydrofuran disolvate with an unknown solvent [O] . Tingting Huang, Haimang Wang, Jianping Zhao 2019

机译：di-cyanido-1：2κ2的合成晶体结构和表征N：C； 2：3κ2C：N-bis（4713162124-hexaoxa-110-diza双环 8.8.8 hexacosane）-1κ8ñ1N10点4O7O13O16岁21岁24;3κ8ñ1N10点4O7O13O16岁21岁24- 5101520-四（4-氯苯基）基卟啉-2κ4N -2-铁（II）-13-二钾（I）四氢呋喃与溶剂的二溶剂化
7. Synthesis of Milbemycins .ALPHA.9, .ALPHA.10, .ALPHA.11, .ALPHA.12, .ALPHA.14, .ALPHA.15, .ALPHA.20, .ALPHA.21, .ALPHA.22, .ALPHA.23, .ALPHA.26, .ALPHA.27, .DELTA.2,3,.DELTA.4,26-Milbemycins A3, A4 from Milbemycins A3, A4, and Their Acaricidal Activities. [O] . TAKAHIRO TSUKIYAMA, HISAKI KAJINO, FUMIE KAJINO, 2002

机译：孤立米尔巴米斯.Alpha.9，.alpha.10，.alpha.11，.alpha.12，.alpha.12，.alpha.15，.alpha.10，.alpha.20，.alpha.20，.alpha.21，.alpha.22，.alpha .23，.alpha.26，.alpha.27，.delta.2,3，.delta.4,26-milbemycins A3，A4来自Milbemycins A3，A4及其杀螨活动。

A general method for the synthesis of bastaranes and isobastaranes: First total synthesis of bastadins 5, 10, 12, 16, 20, and 21

摘要

著录项

相似文献

相关主题

期刊订阅