采用串联 Ichikawa/Winstein 重排反应实现 Jogyamycin 的全合成进展。
Progress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement.
机构信息
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
出版信息
Org Lett. 2023 Nov 24;25(46):8279-8283. doi: 10.1021/acs.orglett.3c03286. Epub 2023 Nov 9.
Abstract
Jogyamycin is a densely functionalized aminocyclopentitol that displays potent antiprotozoal activity. Herein, we report a route toward this natural product that utilizes an unprecedented transformation involving a tandem Ichikawa-Winstein rearrangement to install the C-1/C-2 diamine core. Attempts to further functionalize the C-3/C-4 alkene en route to jogyamycin are also discussed.
摘要
聚醚菌素是一种高度功能化的氨基环戊糖醇，具有很强的抗原生动物活性。在此，我们报告了一条通向该天然产物的路线，该路线利用了一种前所未有的 Ichikawa-Winstein 重排串联反应来构建 C-1/C-2 二胺核心。还讨论了在聚醚菌素路线中进一步官能化 C-3/C-4 烯烃的尝试。
相似文献
1
Progress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement.采用串联 Ichikawa/Winstein 重排反应实现 Jogyamycin 的全合成进展。
Org Lett. 2023 Nov 24;25(46):8279-8283. doi: 10.1021/acs.orglett.3c03286. Epub 2023 Nov 9.
2
Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.通过 Ichikawa 重排反应立体选择性合成聚醚类抗生素柔红霉素的氨基环戊醇核心部分。
J Org Chem. 2019 Nov 1;84(21):14092-14100. doi: 10.1021/acs.joc.9b02249. Epub 2019 Oct 16.
3
Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.通过丙二烯氮杂环丙烷化策略非对映选择性合成交沙霉素的氨基环醇核心。
Org Lett. 2016 Jan 15;18(2):284-7. doi: 10.1021/acs.orglett.5b03453. Epub 2016 Jan 7.
4
Strategies for the Syntheses of Pactamycin and Jogyamycin.巴卡汀和柔红霉素的合成策略。
Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14252-14271. doi: 10.1002/anie.202004560. Epub 2021 Jan 18.
5
Synthesis of the Aminocyclitol Core of Jogyamycin via an Enantioselective Pd-Catalyzed Trimethylenemethane (TMM) Cycloaddition.通过对映选择性钯催化三甲基烯丙基甲烷（TMM）环加成反应合成聚醚类抗生素柔红霉素的氨基环醇核心
Org Lett. 2018 Jul 6;20(13):3938-3942. doi: 10.1021/acs.orglett.8b01518. Epub 2018 Jun 25.
6
Enantioselective synthesis of pactamycin, a complex antitumor antibiotic.对 pactamycin，一种复杂的抗肿瘤抗生素的对映选择性合成。
Science. 2013 Apr 12;340(6129):180-2. doi: 10.1126/science.1234756.
7
Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.朝向 Amphidinolide C1 的合成研究：C(1)-C(15) 片段的立体选择性构建。
Org Lett. 2020 Dec 4;22(23):9174-9177. doi: 10.1021/acs.orglett.0c03134. Epub 2020 Nov 12.
8
Synthesis of the Cyclopentane Core Skeleton of Cranomycin and Jogyamycin.克拉霉素和乔加霉素环戊烷核心骨架的合成。
Org Lett. 2024 Apr 19;26(15):2945-2948. doi: 10.1021/acs.orglett.4c00491. Epub 2024 Apr 3.
9
Regio- and diastereoselective access to densely functionalized ketones the Boekelheide rearrangement of isoxazoline -oxides.区域和非对映选择性合成多官能团化酮——异恶唑啉氧化物的博克尔海德重排反应
Org Biomol Chem. 2022 Jul 20;20(28):5624-5637. doi: 10.1039/d2ob00787h.
10
E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing.用于天然产物合成和骨架编辑的 E-和 Z-三取代大环烯烃。
Nat Chem. 2022 Jun;14(6):640-649. doi: 10.1038/s41557-022-00935-y. Epub 2022 May 16.
本文引用的文献
1
Two-Phase Synthesis of Taxol.紫杉醇的两相合成。
J Am Chem Soc. 2020 Jun 10;142(23):10526-10533. doi: 10.1021/jacs.0c03592. Epub 2020 May 29.
2
Strategies for the Syntheses of Pactamycin and Jogyamycin.巴卡汀和柔红霉素的合成策略。
Angew Chem Int Ed Engl. 2021 Jun 21;60(26):14252-14271. doi: 10.1002/anie.202004560. Epub 2021 Jan 18.
3
Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.通过 Ichikawa 重排反应立体选择性合成聚醚类抗生素柔红霉素的氨基环戊醇核心部分。
J Org Chem. 2019 Nov 1;84(21):14092-14100. doi: 10.1021/acs.joc.9b02249. Epub 2019 Oct 16.
4
On the Winstein rearrangement: equilibrium and mechanism.关于温斯坦重排：平衡与机理。
ARKIVOC. 2019;2019(1):1-17. doi: 10.24820/ark.5550190.p010.819. Epub 2019 Mar 30.
5
Allylic azides: synthesis, reactivity, and the Winstein rearrangement.烯丙基叠氮化物：合成、反应性和温斯坦重排。
Org Biomol Chem. 2019 May 8;17(18):4406-4429. doi: 10.1039/c8ob03178a.
6
Synthesis of the Aminocyclitol Core of Jogyamycin via an Enantioselective Pd-Catalyzed Trimethylenemethane (TMM) Cycloaddition.通过对映选择性钯催化三甲基烯丙基甲烷（TMM）环加成反应合成聚醚类抗生素柔红霉素的氨基环醇核心
Org Lett. 2018 Jul 6;20(13):3938-3942. doi: 10.1021/acs.orglett.8b01518. Epub 2018 Jun 25.
7
Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement.Winstein 重排反应中存在(sigmatropic)和离子途径的证据。
J Org Chem. 2018 Aug 3;83(15):8214-8224. doi: 10.1021/acs.joc.8b00961. Epub 2018 Jun 14.
8
Fluorinated Amine Stereotriads via Allene Amination.通过丙二烯胺化反应合成全氟胺立体三联体。
Org Lett. 2017 Jun 16;19(12):3239-3242. doi: 10.1021/acs.orglett.7b01342. Epub 2017 Jun 2.
9
Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.通过丙二烯氮杂环丙烷化策略非对映选择性合成交沙霉素的氨基环醇核心。
Org Lett. 2016 Jan 15;18(2):284-7. doi: 10.1021/acs.orglett.5b03453. Epub 2016 Jan 7.
10
Novel Pactamycin Analogs Induce p53 Dependent Cell-Cycle Arrest at S-Phase in Human Head and Neck Squamous Cell Carcinoma (HNSCC) Cells.新型派达霉素类似物在人头颈鳞状细胞癌（HNSCC）细胞中诱导p53依赖性细胞周期在S期停滞。
PLoS One. 2015 May 4;10(5):e0125322. doi: 10.1371/journal.pone.0125322. eCollection 2015.
Zotero 插件