Article
Chemistry, Multidisciplinary
Hironobu Hojo, Toshiki Takei, Yuya Asahina, Nobuaki Okumura, Toshifumi Takao, Masatomo So, Isao Suetake, Takeshi Sato, Akihiro Kawamoto, Yoshio Hirabayashi
Summary: In this study, the essential protein Caveolin-1 for caveola formation was chemically synthesized and successfully inserted into the lipid bilayer to form a V-shaped structure. The solid-phase method was used to synthesize peptide segments, and O-acyl isopeptide structures were incorporated to improve solubility. After ligation by the thioester method and the introduction of palmitoyl groups, the obtained polypeptide was inserted into bicelles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xu Gong, Juan Huang, Xiangrui Sun, Ziling Chen, Ming Yang
Summary: Illicium sesquiterpenes, a family of biologically active secondary metabolites, have been synthesized using a comprehensive biosynthetic pathway and a synthetic route to illisimonin A and merrilactone A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Majid M. Heravi, Batoul Alipour, Vahideh Zadsirjan, Masoume Malmir
Summary: The Robinson annulation is a significant reaction for the synthesis of alpha,beta-unsaturated ketone ring that involves the generation of two C-C bonds. It has been frequently used in the total synthesis of biologically active natural products. These products and their derivatives play a major role in pharmacotherapy, especially for cancer and infectious diseases.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ya-Kui Sun, Jin-Bao Qiao, Yu-Meng Xin, Qin Zhou, Zhi-Hua Ma, Hui Shao, Yu-Ming Zhao
Summary: A concise and divergent synthesis of the complex hasubanan alkaloids metaphanine and oxoepistephamiersine from commercially available and inexpensive cyclohexanedione monoethylene acetal was reported. The synthesis includes a palladium-catalyzed cascade cyclization reaction, a regioselective Baeyer-Villiger oxidation followed by a MeNH2 triggered skeletal reorganization cascade, and a strategically late-stage regio-/diastereoselective oxidative annulation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ya-Kui Sun, Jin-Bao Qiao, Yu-Meng Xin, Qin Zhou, Zhi-Hua Ma, Hui Shao, Yu-Ming Zhao
Summary: In this paper, a concise and divergent synthesis of the complex hasubanan alkaloids metaphanine and oxoepistephamiersine from commercially available and inexpensive cyclohexanedione monoethylene acetal is reported. The synthesis involves a palladium-catalyzed cascade cyclization reaction, regioselective Baeyer-Villiger oxidation followed by a MeNH2 triggered skeletal reorganization cascade, and a strategically late-stage regio-/diastereoselective oxidative annulation of sp(3) C-H bond. Additionally, a highly enantioselective alkylation of cyclohexanedione monoethylene acetal was used for the asymmetric synthesis of the target molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chao Chen, Ru-Xin Liu, Feng Xiong, Zi-Hao Li, Jun-Chen Kang, Tong-Mei Ding, Shu-Yu Zhang
Summary: This study demonstrates the utilization of Freon-type methanes as functional one-carbon synthons in the synthesis of various deuterated indoline alkaloids. Halomethyl radicals are generated through electro-reductive C-X cleavage of Freon-type methanes and efficiently captured by acrylamides, providing halogenated oxindoles through radical cyclization. The reaction shows good tolerance towards functional groups and allows for facile introduction of deuterium and fluorine atoms from Freon-type methanes. Further transformation of halogenated oxindoles enables the synthesis of many bioactive drug molecules and skeletons, including deuterated (+/-)-physostigmine, deuterated (+/-)-esermethole, and deuterated (+/-)-lansai B.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Priyanka Kataria, Rajesh Nomula, Ravindar Kontham
Summary: This study describes the total synthesis of ent-rhoiptelol B through two distinct synthetic strategies, providing insights into designing novel synthetic routes for THP-DAH-derived natural products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Qian Rao, Yan Zhang, Xin-Yu Gu, Yin-Ping Liu, Bo Jiang, Wen-Juan Hao
Summary: This paper reports a new gold self-relay catalysis method, enabling intramolecular annulation and intermolecular Michael addition of 3-yne-1,2-diols with aurone-derived azadienes (or para-quinone methides), efficiently producing a range of unsymmetrical furanized triarylmethanes with substituent diversity in good yields. The overall process is governed by the & pi;- and & sigma;-Lewis acid capability of gold complexes, providing a catalytic strategy for constructing triarylmethane skeletons.
Article
Chemistry, Organic
Luke R. Odell, Bobo Skillinghaug, Christof Matt, Peng Wu, Tobias Koolmeister, Matthieu Desroses, Sabin Llona-Minguez, Olov Wallner, Thomas Helleday, Martin Scobie
Summary: Here, we describe the development of a new cascade reaction for the synthesis of rare indazole acetic acid scaffolds. By heating 3-amino-3-(2-nitroaryl)propanoic acids with an appropriate nucleophile/solvent under basic conditions, three distinct indazole acetic acid derivatives (unsubstituted, hydroxy, and alkoxy) can be conveniently synthesized. The reaction can tolerate various functional groups and electronic effects, resulting in the synthesis and characterization of 23 novel indazole acetic acids. This work provides a valuable synthetic strategy for drug discovery programs.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yi-Peng Zhang, Shufei Du, Ying Ma, Weixin Zhan, Wen Chen, Xiaodong Yang, Hongbin Zhang
Summary: In this study, we present a structure-unit-based asymmetric total synthesis of sinulochmodin C, a norcembranoid diterpenoid with a unique structure. Our synthetic route involves several key reactions, including intramolecular double Michael addition, vinylogous hydroxylation/oxidation, transannular oxa-Michael addition, and bioinspired transformation. The successful total synthesis of sinulochmodin C demonstrates the effectiveness of our approach.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xueying Wang, Phang Yee Lin, Changwu Zheng, Hongxi Xu
Summary: Xanthochymol, a PPAP natural compound, was synthesized from 3,3-dimethylglutaric acid in 11 steps with a total yield of 10%, providing references for future research on its side chain isomers.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Dapeng Zhu, Mingyu Geng, Biao Yu
Summary: Starfish have developed a special type of secondary metabolite called starfish saponins to defend against predators and parasites. Among them, starfish cyclic steroid glycosides are structurally unique and pose a significant synthetic challenge.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Itaru Suzuki, Kazuki Ogura, Jun-ya Shimazu, Ikuya Shibata
Summary: The MgX2-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes resulted in high yields of oxaspiro[2.5]octenes. The rare intramolecular oxa-Michael addition of Mg enolate was found to be the key step in the reaction, with the oxaspiro ring being transformed into 4H-pyran at higher temperatures in the presence of MgX2.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sagar S. Thorat, Gamidi Rama Krishna, Ravindar Kontham
Summary: This study describes the efforts towards the stereoselective total synthesis of (+/-)-pleurospiroketals A and B, utilizing specific key building blocks and substrate-controlled stereoselection. The initially planned synthetic route was found to be insurmountable, leading to the identification of a reliable strategy involving various key steps.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Chenikkayala Siva Sankara, Shweta Prakash Gaikwad, Irishi N. N. Namboothiri
Summary: In this Account, recent advancements in Hauser-Kraus (H-K) annulation for the synthesis of natural products and various functionalized carbocycles and heterocycles are summarized. Besides the classical H-K annulation between a 1,4-dipolar synthon and a 1,2-dipolar synthon, alternative annulation modes like [4+4] and [4+1], as well as other reactivities of 3-nucleophilic phthalides, are discussed.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
