☆ 4.8 Article

Total Synthesis of (+)-Vicenin-2

ORGANIC LETTERS (2016)

期刊

ORGANIC LETTERS

卷 18, 期 18, 页码 4488-4490

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.6b02203

关键词

-

类别

Chemistry, Organic

资金

JSPS KAKENHI [JP23000006, JP16H06351, JP16H01137, JP16H04107]
Grants-in-Aid for Scientific Research [16H01137, 16H04107] Funding Source: KAKEN

向作者/读者索取更多资源

Protocol

Reagent

摘要

The bis-C-glucosyl flavonoid vicenin-2 (1) has been synthesized by exploiting bis-C-glycosylation of 1,3,5-trifluorobenzene and aromatic nucleophilic substitution to transform fluorine atoms to oxygen functions in excellent yield.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Organic

Asymmetric Total Synthesis of Amphirionin-2

Dhiman Saha, Gour Hari Mandal, Rajib Kumar Goswami

Summary: A convergent route has been developed for the asymmetric total synthesis of potent anticancer polyketide natural product amphirionin-2, with key features including Sharpless asymmetric dihydroxylation, cycloetherification, Wittig olefination, Julia-Kocienski olefination, and Crimmins propionate aldol reaction after the proposed structures of amphirionin-2 were revised based on a recent report.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of Cochlearol B via Intramolecular [2+2] Photocycloaddition

Tomoya Mashiko, Yuta Shingai, Jun Sakai, Shogo Kamo, Shinya Adachi, Akinobu Matsuzawa, Kazuyuki Sugita

Summary: In this study, the first total synthesis of cochlearol B, a meroterpenoid natural product with a unique pentacyclic structure, was described. Key steps including oxidative cyclization and subsequent intramolecular [2+2] photocycloaddition allowed efficient access to cochlearol B with a longest linear sequence of 16 steps and 9% overall yield. Single-crystal X-ray crystallographic analysis confirmed the stereochemistry of cochlearol B.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Mutilin: A Transannular [2+2] Cycloaddition/Fragmentation Approach

Han Chen, Zesheng Li, Peng Shao, Haosen Yuan, Si-Cong Chen, Tuoping Luo

Summary: A new and enantioselective total synthesis of the diterpenoid (+)-mutilin is described, which involves the Claisen rearrangement, transannular [2+2] photocycloaddition, ring-opening reaction, and subsequent late-stage alkylations and reduction to forge the characteristic skeleton.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total synthesis and complete configurational assignment of amphirionin-2

Shota Kato, Daichi Mizukami, Tomoya Sugai, Masashi Tsuda, Haruhiko Fuwa

Summary: This study reports the first total synthesis of amphirionin-2, determination of its absolute configuration, and reassignment of certain relative configurations. The synthesis involved cobalt-catalyzed cyclization of gamma-hydroxy olefins and a late-stage Stille-type coupling, leading to the successful production and comparison of four candidate diastereomers.

CHEMICAL SCIENCE (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total synthesis of interleukin-2 via a tunable backbone modification strategy

Hongxiang Wu, Yi Tan, Wai Lok Ngai, Xuechen Li

Summary: Chemical synthesis of hydrophobic proteins is challenging, but can be achieved by integrating peptide solubilizing strategies with peptide ligation. This study presents a tunable backbone modification strategy that allows for the introduction of a solubilizing tag for peptide purification and ligation processes. The effectiveness of this strategy was demonstrated by the chemical synthesis of interleukin-2.

CHEMICAL SCIENCE (2023)

添加到收藏夹

Article Multidisciplinary Sciences

Total synthesis of himastatin

Kyan A. D'Angelo, Carly K. Schissel, Bradley L. Pentelute, Mohammad Movassaghi

Summary: The study presents a concise total synthesis method for himastatin, a natural product with an unusual homodimeric structure. The final-stage dimerization strategy used in the synthesis was inspired by a detailed understanding of the compound's biogenesis. By combining this approach with a modular synthesis, a series of designed derivatives of himastatin, including synthetic probes to investigate its antibiotic activity, were efficiently accessed.

SCIENCE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Allenamide-Initiated Cascade [2+2+2] Annulation Enabling the Divergent Total Synthesis of (-)-Deoxoapodine, (-)-Kopsifoline D and (±)-Melotenine A

Liu-Peng Zhao, Peng-Juan Li, Lijia Wang, Yong Tang

Summary: A facile method for the construction of the aspidosperma core from indoles functionalized with a nonterminal N-allenamide and dimethyl methylenemalonate is described. The annulation reaction provides straightforward access to the tetracyclic spiroindoline skeleton with substituents at the C5 position occurring in many natural products. As an application of this reaction, the total synthesis of three important natural products was possible in short routes from tryptamine.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of Kibdelomycin

Chi He, Yu Wang, Cheng Bi, David S. Peters, Timothy J. Gallagher, Johannes Teske, Jason S. Chen, Rachel Corsetti, Anthony D'Onofrio, Kim Lewis, Phil S. Baran

Summary: A modular total synthesis method for kibdelomycin has been disclosed, which allows for structure-activity relationship studies. This method uses simple building blocks and addresses lingering questions regarding its structural assignment and its relationship to amycolamicin. Initial antibacterial assays indicate that both C-22 epimers of the natural product exhibit similar activity, while structurally truncated analogs lose activity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of (-)-Arborisidine

Feng-Yuan Wang, Lei Jiao

Summary: An asymmetric total synthesis of cage-like indole alkaloid arborisidine is achieved using a new synthetic strategy that involves a catalytic parallel kinetic resolution based on ambident nucleophilicity of indole and a 5-exo-trig radical cyclization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of Aleutianamine

Hao Yu, Zachary P. Sercel, Samir P. Rezgui, Jonathan Farhi, Scott C. Virgil, Brian M. Stoltz

Summary: This study describes a synthetic approach to aleutianamine and highlights its potent biological activity against human pancreatic cancer cells, making it a potential candidate for therapeutic development.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of Resiniferatoxin

Vasil H. Vasilev, Lukas Spessert, Kuan Yu, Thomas J. Maimone

Summary: The large family of daphnane diterpene orthoesters (DDOs) represents a remarkable class of natural products both in terms of structure and function. They are potent lead compounds for the treatment of pain, neurodegeneration, HIV/AIDS, and cancer. However, the synthesis of DDO natural products remains rare.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Aberrarone

Yang Wang, Yongjian Su, Yanxing Jia

Summary: In this research, the structurally intriguing diterpene (+)-aberrarone was synthesized in only 12 steps from commercially available (S,S)-carveol without protecting group manipulations. This concise synthesis includes a Cu-catalyzed asymmetric hydroboration to generate the chiral methyl group, a Ni-catalyzed reductive coupling to link two fragments, and a Mn-mediated radical cascade cyclization to construct the triquinane system.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of Vilmoraconitine

Jiujian Ji, Jiajun Chen, Sixun Qin, Wanye Li, Jun Zhao, Guozhao Li, Hao Song, Xiao-Yu Liu, Yong Qin

Summary: This article reports the first total synthesis of vilmoraconitine using efficient ring-forming reactions. Key steps include an oxidative dearomatization-induced Diels-Alder cycloaddition, a hydrodealkenylative fragmentation/Mannich sequence, and an intramolecular Diels-Alder cycloaddition.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of Limaol

Stephan N. Hess, Xiaobin Mo, Conny Wirtz, Alois Fuerstner

Summary: Limaol, a marine-derived C40-polyketide, is unique in structure due to the nonthermodynamic array of four skipped methylene substituents on its hydrophobic tail. This distinctive segment was assembled using a two-directional approach and coupled to the polyether domain through an allyl/alkenyl Stille reaction under neutral conditions. The core region was prepared through several key steps, including asymmetric propargylation catalyzed by 3,3'-dibromo-BINOL, gold-catalyzed spirocyclization, and substrate-controlled allylation to introduce the southern sector.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total Synthesis of (+)-Shearilicine

Daria E. Kim, Yingchuan Zhu, Shingo Harada, Isaiah Aguilar, Abbigayle E. Cuomo, Minghao Wang, Timothy R. Newhouse

Summary: In this study, we successfully reported the total synthesis of the indole diterpenoid natural product shearilicine for the first time through an 11-step sequence using a generalizable precursor. The target molecule was obtained in an enantiospecific manner using a native chiral auxiliary strategy. The formation of the key carbazole substructure was achieved through a mild intramolecular Heck cyclization, which was promoted by noncovalent substrate-ligand and ligand-ligand interactions revealed by computational study.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Chemistry, Organic

C1′-Azacycloalkyl Hexahydrocannabinols

Thanh C. Ho, Naoyuki Shimoda, Marcus A. Tius, Spyros P. Nikas, Wen Zhang, Alexandros Makriyannis

JOURNAL OF ORGANIC CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Organic

Enantioselective Access to Bicyclo[3.2.1]octadienone Skeleton: Total Syntheses of (+)-Engelharquinone and Its Epoxide

Takumi Fukazawa, Yoshio Ando, Ken Ohmori, Tamio Hayashi, Keisuke Suzuki

ORGANIC LETTERS (2017)

添加到收藏夹

Article Chemistry, Organic

Total Syntheses of Atrovenetin and Atrovenetinone: A Naphtha-lene-Annulation Approach to a Discoid Tricycle Using Allenic Acid

Kyohei Matsushita, Keisuke Suzuki, Ken Ohmori

SYNLETT (2017)

添加到收藏夹

Article Chemistry, Organic

Total Syntheses of Pusilatins A-C, Liverwort-Derived Macrocyclic Bisbibenzyl Dimers

Takahiro Yamada, Hiromu Takiguchi, Ken Ohmori, Keisuke Suzuki

ORGANIC LETTERS (2018)

添加到收藏夹

Article Chemistry, Organic

Total Synthesis of Selligueain A, a Sweet Flavan Trimer

Yuka Noguchi, Rikako Takeda, Keisuke Suzuki, Ken Ohmori

ORGANIC LETTERS (2018)

添加到收藏夹

Article Plant Sciences

Impact of Green Tea Catechin ECG and Its Synthesized Fluorinated Analogue on Prostate Cancer Cells and Stimulated Immunocompetent Cells

Sven Stadlbauer, Carmen Steinborn, Amy Klemd, Fumihiko Hattori, Ken Ohmori, Keisuke Suzuki, Roman Huber, Philipp Wolf, Carsten Gruendemann

PLANTA MEDICA (2018)

添加到收藏夹

Article Chemistry, Organic

First Total Synthesis of Oxirapentyn D, a Highly Oxidized Chromene Natural Product

Takahiro Sakai, Keisuke Suzuki, Ken Ohmori

SYNLETT (2018)

添加到收藏夹

Article Chemistry, Organic

Synthesis and structures of alpha-lithiated vinyl ethers

Thanh C. Ho, Jonathan Congmon, Zhe Zhou, Marcus A. Tius, Lawrence M. Pratt

TETRAHEDRON (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Oxygenated ortho-Methylbenzaldehydes via Aryne [2+2] Cycloaddition and Benzocyclobutenol Ring Opening

Mark M. Maturi, Ken Ohmori, Keisuke Suzuki

CHIMIA (2018)

添加到收藏夹

Article Chemistry, Organic

Synthetic Studies on Flavan-Derived Natural Polyphenols: a Complex Molecular Platform in Organic Synthesis

Ken Ohmori

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN (2018)

添加到收藏夹

Article Biochemistry & Molecular Biology

Chain Substituted Cannabilactones with Selectivity for the CB2 Cannabinoid Receptor

Shakiru O. Alapafuja, Spyros P. Nikas, Thanh C. Ho, Fei Tong, Othman Benchama, Alexandros Makriyannis

MOLECULES (2019)

添加到收藏夹

Article Biochemistry & Molecular Biology

Synthesis of Functionalized Cannabilactones

Yingpeng Liu, Thanh C. Ho, Mohammed Baradwan, Maria Pascual Lopez-Alberca, Christos Iliopoulos-Tsoutsouvas, Spyros P. Nikas, Alexandros Makriyannis

MOLECULES (2020)

添加到收藏夹

Article Chemistry, Medicinal

Oxa-adamantyl cannabinoids

Thanh C. Ho, Marcus A. Tius, Spyros P. Nikas, Ngan K. Tran, Fei Tong, Han Zhou, Nikolai Zvonok, Alexandros Makriyannis

Summary: The novel oxa-adamantyl cannabinoids are identified as high affinity ligands for CB1 and CB2 cannabinoid receptors, showing potential as potent CB1 receptor agonists. Their synthesis is convenient, amenable to scale up, and suitable for large-scale preparation.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Blockade of CB1 or Activation of CB2 Cannabinoid Receptors Is Differentially Efficacious in the Treatment of the Early Pathological Events in Streptozotocin-Induced Diabetic Rats

Dimitris Spyridakos, Niki Mastrodimou, Kiran Vemuri, Thanh C. C. Ho, Spyros P. P. Nikas, Alexandros Makriyannis, Kyriaki Thermos

Summary: Oxidative stress, neurodegeneration, neuroinflammation, and vascular leakage are involved in the early stage of diabetic retinopathy (ESDR). This study investigated the therapeutic potential of blocking CB1R and activating CB2R for treating early toxic events in DR. The results suggest that CB2R activation, CB1R blockade, and dual treatment can attenuate nitrative stress induced by diabetes, protect neural elements, and reduce vascular leakage.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2023)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.