氮杂螺旋酸-1的ABCD和ABCDE环系的合成。
Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1.
作者信息
Zhou Xiao-Ti, Carter Rich G
机构信息
Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR 97331, USA.
出版信息
Chem Commun (Camb). 2004 Oct 7(19):2138-40. doi: 10.1039/b410092a. Epub 2004 Sep 20.
Abstract
The efficient syntheses of the ABCD ring system of the originally proposed structure of azaspiracid-1 and the ABCDE ring system of the revised structure of azaspiracid-1 containing the correct stereochemistry at C(6), C(10), C(13), C(14), C(16), C(17), C(19), C(21), C(22), C(24) and C(25) have been achieved.
摘要
已实现氮杂螺旋酸-1最初提出结构的ABCD环系以及氮杂螺旋酸-1修正结构的ABCDE环系的高效合成，该修正结构在C(6)、C(10)、C(13)、C(14)、C(16)、C(17)、C(19)、C(21)、C(22)、C(24)和C(25)处具有正确的立体化学结构。
相似文献
1
Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1.氮杂螺旋酸-1的ABCD和ABCDE环系的合成。
Chem Commun (Camb). 2004 Oct 7(19):2138-40. doi: 10.1039/b410092a. Epub 2004 Sep 20.
2
Structural revision and total synthesis of azaspiracid-1, part 2: definition of the ABCD domain and total synthesis.氮杂螺旋酸-1的结构修正与全合成，第2部分：ABCD结构域的定义与全合成
Angew Chem Int Ed Engl. 2004 Aug 20;43(33):4318-24. doi: 10.1002/anie.200460696.
3
Total synthesis and structural elucidation of azaspiracid-1. Final assignment and total synthesis of the correct structure of azaspiracid-1.azaspiracid-1的全合成与结构解析。azaspiracid-1正确结构的最终确定与全合成。
J Am Chem Soc. 2006 Mar 8;128(9):2859-72. doi: 10.1021/ja054750q.
4
Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: an iodoetherification-dehydroiodination strategy for complex spiroketals.azaspiracid-1的ABCD三氧杂双螺缩酮亚基的合成：一种用于复杂螺缩酮的碘醚化-脱碘化氢策略。
Org Lett. 2007 Oct 11;9(21):4303-6. doi: 10.1021/ol701866v. Epub 2007 Sep 20.
5
Total synthesis and structural elucidation of azaspiracid-1. Construction of key building blocks for originally proposed structure.azaspiracid-1的全合成与结构解析。为最初提出的结构构建关键构建模块。
J Am Chem Soc. 2006 Feb 22;128(7):2244-57. doi: 10.1021/ja0547477.
6
Total synthesis of (+)-azaspiracid-1. Part I: Synthesis of the fully elaborated ABCD aldehyde.（+）-氮杂螺旋酸-1的全合成。第一部分：全官能化ABCD醛的合成。
Angew Chem Int Ed Engl. 2007;46(25):4693-7. doi: 10.1002/anie.200701515.
7
Structural revision and total synthesis of azaspiracid-1, part 1: intelligence gathering and tentative proposal.azaspiracid-1的结构修正与全合成，第1部分：情报收集与初步提议
Angew Chem Int Ed Engl. 2004 Aug 20;43(33):4312-8. doi: 10.1002/anie.200460695.
8
Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.氮杂螺旋酸-1的南部FGHI环系的合成以及对C28-和C36-酮缩合控制因素的研究。
Angew Chem Int Ed Engl. 2006 Nov 20;45(45):7622-6. doi: 10.1002/anie.200603353.
9
Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3.氮杂螺旋酸-2和氮杂螺旋酸-3的全合成及修正结构的确证
Angew Chem Int Ed Engl. 2006 Apr 10;45(16):2609-15. doi: 10.1002/anie.200600295.
10
Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.（+）-氮杂螺旋酸-1的全合成。复杂分子合成复杂性的展示。
J Am Chem Soc. 2008 Dec 3;130(48):16295-309. doi: 10.1021/ja804659n.
引用本文的文献
1
Iriomoteolides: novel chemical tools to study actin dynamics.西表岛大环内酯类化合物：研究肌动蛋白动力学的新型化学工具。
Chem Sci. 2018 Apr 3;9(15):3793-3802. doi: 10.1039/c7sc04286h. eCollection 2018 Apr 21.
2
Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1.海洋生物毒素氮杂螺旋酸-1的ABC三氧杂双螺缩酮亚基的合成与计算研究
Nat Prod Commun. 2008 Nov;3(11):1771-1780.
3
Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.通过五氯化铌和五溴化铌介导的醇盐重排合成烯丙基卤化物和联烯基卤化物
J Org Chem. 2009 Oct 2;74(19):7294-9. doi: 10.1021/jo901287f.
4
Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.（+）-氮杂螺旋酸-1的全合成。复杂分子合成复杂性的展示。
J Am Chem Soc. 2008 Dec 3;130(48):16295-309. doi: 10.1021/ja804659n.
5
Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.氮杂螺旋酸-1的南部FGHI环系的合成以及对C28-和C36-酮缩合控制因素的研究。
Angew Chem Int Ed Engl. 2006 Nov 20;45(45):7622-6. doi: 10.1002/anie.200603353.
6
Synthesis of the C1-C26 northern portion of azaspiracid-1: kinetic versus thermodynamic control of the formation of the bis-spiroketal.azaspiracid-1的C1-C26北部片段的合成：双螺缩酮形成的动力学与热力学控制
Angew Chem Int Ed Engl. 2006 Mar 3;45(11):1787-90. doi: 10.1002/anie.200503733.
本文引用的文献
1
Structural revision and total synthesis of azaspiracid-1, part 2: definition of the ABCD domain and total synthesis.氮杂螺旋酸-1的结构修正与全合成，第2部分：ABCD结构域的定义与全合成
Angew Chem Int Ed Engl. 2004 Aug 20;43(33):4318-24. doi: 10.1002/anie.200460696.
2
Structural revision and total synthesis of azaspiracid-1, part 1: intelligence gathering and tentative proposal.azaspiracid-1的结构修正与全合成，第1部分：情报收集与初步提议
Angew Chem Int Ed Engl. 2004 Aug 20;43(33):4312-8. doi: 10.1002/anie.200460695.
3
Total synthesis of the proposed azaspiracid-1 structure, part 2: coupling of the C1-C20, C21-C27, and C28-C40 fragments and completion of the synthesis.所提出的azaspiracid-1结构的全合成，第2部分：C1-C20、C21-C27和C28-C40片段的偶联及合成的完成。
Angew Chem Int Ed Engl. 2003 Aug 11;42(31):3649-53. doi: 10.1002/anie.200351826.
4
Total synthesis of the proposed azaspiracid-1 structure, part 1: construction of the enantiomerically pure C1-C20, C21-C27, and C28-C40 fragments.所提出的azaspiracid-1结构的全合成，第1部分：对映体纯的C1-C20、C21-C27和C28-C40片段的构建。
Angew Chem Int Ed Engl. 2003 Aug 11;42(31):3643-8. doi: 10.1002/anie.200351825.
5
Geographical, temporal, and species variation of the polyether toxins, azaspiracids, in shellfish.贝类中聚醚毒素——azaspiracids的地理、时间和物种变异情况。
Environ Sci Technol. 2003 Jul 15;37(14):3078-84. doi: 10.1021/es020246z.
6
Ubiquitous 'benign' alga emerges as the cause of shellfish contamination responsible for the human toxic syndrome, azaspiracid poisoning.无处不在的“良性”藻类成为导致贝类污染的原因，而贝类污染会引发人类中毒综合征——azaspiracid中毒。
Toxicon. 2003 Feb;41(2):145-51. doi: 10.1016/s0041-0101(02)00244-1.
8
Boron-mediated aldol reaction of carboxylic esters: complementary anti- and syn-selective asymmetric aldol reactions.硼介导的羧酸酯的羟醛反应：互补的反式和顺式选择性不对称羟醛反应
J Org Chem. 2002 Jul 26;67(15):5250-6. doi: 10.1021/jo0257896.
9
First evidence of an extensive northern European distribution of azaspiracid poisoning (AZP) toxins in shellfish.贝类中出现氮杂螺旋酸酯中毒（AZP）毒素在北欧广泛分布的首个证据。
Toxicon. 2002 Jul;40(7):909-15. doi: 10.1016/s0041-0101(02)00082-x.
10
Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.azaspiracid的ABC环系统的合成。2. 关于C(16)和C(17)取代对双螺环化作用影响的系统研究。
Org Lett. 2002 Jun 27;4(13):2181-4. doi: 10.1021/ol026034o.
Zotero 插件