Article
Chemistry, Multidisciplinary
Nicholas J. Foy, Sergey V. Pronin
Summary: This paper describes the synthesis of a potent inhibitor of bacterial protein synthesis, pleuromutilin. The assembly of the critical cyclooctane fragment is achieved through an oxidative ring-expansion, and the complete stereochemical relay in the synthetic sequence is enabled by the careful choice of tactics. The necessary connectivity pattern of the perhydroindanone motif is rapidly established through a sequence of cycloaddition and radical cyclization events. By applying this strategy, the target natural product can be prepared in 16 steps from commercially available materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Hu Tang, Xiaohong Yuan, Yong Cheng, Hongzhan Fei, Fuyang Liu, Tao Liang, Zhidan Zeng, Takayuki Ishii, Ming-Sheng Wang, Tomoo Katsura, Howard Sheng, Huiyang Gou
Summary: The study describes the synthesis, structural characterization, and formation mechanism of a paracrystalline state of diamond, adding an unusual form of diamond to the family of carbon-based materials.
Article
Chemistry, Multidisciplinary
Annie R. Hooper, Andraz Ostrek, Ana Milian-Lopez, David Sarlah
Summary: This study presents a chemical synthesis method for preparing pyritide A2, involving the synthesis of a pyridine ring from an amino acid precursor, resulting in the efficient preparation of this class of natural products and analogues.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yanyu Chen, Zhengyuan Xin, Hui Wang, Haibing He, Shuanhu Gao
Summary: Zoanthamine alkaloids are structurally unique and complex natural products that have a broad range of biological activities and potential in drug discovery. The synthesis of norzoanthamine and the core structure of zoanthenol have been studied, focusing on the construction of challenging adjacent stereocenters using radical reactions as key steps. The research provides insights into the biological profile of norzoanthamine and expands the understanding of zoanthamine alkaloids.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Multidisciplinary Sciences
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.
Article
Chemistry, Multidisciplinary
Georg Spaeth, Alois Fuerstner
Summary: The introduction of aldgarose sugar to the C5-OH group of the macrocyclic aglycone of aldgamycin N is difficult. Hence, a revised synthesis route was used, and a new scalable method for the synthesis of this sugar was developed to reduce costs. The formation of the glycoside required mild conditions and allowed for late-stage functionalization of the macrolide ring.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Caiyun Chen, Haifeng Lv, Ping Zhang, Zhiwen Zhuo, Yu Wang, Chen Ma, Wenbin Li, Xuguang Wang, Baojie Feng, Peng Cheng, Xiaojun Wu, Kehui Wu, Lan Chen
Summary: Borophene, a novel material composed of boron atoms, has been successfully synthesized as large-size, single-crystalline bilayer on a copper substrate. The bilayer borophene exhibits metallic character and increased resistance to oxidation compared to its monolayer counterparts.
Article
Chemistry, Multidisciplinary
Rui Yang, Zeyu Zhou, Huanfeng Jiang, Toh-Seok Kam, Kai Chen, Zhiqiang Ma
Summary: The first asymmetric total synthesis of the monoterpenoid indole alkaloid arboduridine has been achieved. The synthesis involves several reactions to construct the complex structure and demonstrates a highly enantioselective synthetic strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Multidisciplinary
Martin Tomanik, Zhi Xu, Seth B. Herzon
Summary: This article describes an enantioselective total synthesis of the nonahydroxylated sesquiterpenoid euonyminol, which is the dihydro-flagarofuran nucleus of the macrocyclic terpenoid alkaloids known as the cathedulins. Key features of the synthetic sequence include highly diastereoselective reactions to establish key structural elements, ultimately providing the first synthetic access to enantioenriched euonyminol and establishing a platform for synthesizing the cathedulins.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Organic
Vikram A. Sarpe, Santanu Jana, Suvarn S. Kulkarni
Article
Chemistry, Organic
Manishkumar A. Chaube, Vikram A. Sarpe, Santanu Jana, Suvarn S. Kulkarni
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Medicinal
Amr Sonousi, Vikram A. Sarpe, Margarita Brilkova, Jochen Schacht, Andrea Vasella, Erik C. Boettger, David Crich
ACS INFECTIOUS DISEASES
(2018)
Article
Chemistry, Organic
Vikram A. Sarpe, Suvarn S. Kulkarni
ORGANIC & BIOMOLECULAR CHEMISTRY
(2013)
Article
Chemistry, Organic
Vikram A. Sarpe, Suvarn S. Kulkarni
Article
Chemistry, Organic
Santanu Jana, Vikram A. Sarpe, Suvarn S. Kulkarni
Article
Chemistry, Medicinal
Girish C. Sati, Vikram A. Sarpe, Takayuki Furukawa, Sujit Mondal, Matilde Mantovani, Sven N. Hobbie, Andrea Vasella, Erik C. Bottger, David Crich
ACS INFECTIOUS DISEASES
(2019)
Article
Biochemistry & Molecular Biology
Ruchika Dadhich, Manjari Mishra, Shangbo Ning, Santanu Jana, Vikram A. Sarpe, Jaladhar Mahato, Mojie Duan, Suvarn S. Kulkarni, Shobhna Kapoor
ACS CHEMICAL BIOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Jonathan C. K. Quirke, Parasuraman Rajasekaran, Vikram Sarpe, Amr Sonousi, Ivan Osinnii, Marina Gysin, Klara Haldimann, Qiao-Jun Fang, Dimitri Shcherbakov, Sven N. Hobbie, Su-Hua Sha, Jochen Schacht, Andrea Vasella, Erik C. Boettger, David Crich
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Biochemistry & Molecular Biology
Riku Ogasahara, Shuay Abdullayev, Vikram A. Sarpe, Appi Reddy Mandhapati, David Crich
CARBOHYDRATE RESEARCH
(2020)
Article
Chemistry, Organic
Santanu Jana, Vikram A. Sarpe, Suvarn S. Kulkarni
Summary: In this study, a total synthesis strategy for the structurally unique fungal glycolipid fusaroside was reported, with a proposed revision in its structure, particularly regarding the position of olefins in the lipid chain.
Article
Chemistry, Medicinal
Dimitrijs Lubriks, Rimants Zogota, Vikram A. Sarpe, Takahiko Matsushita, Girish C. Sati, Klara Haldimann, Marina Gysin, Erik C. Boettger, Andrea Vasella, Edgars Suna, Sven N. Hobbie, David Crich
Summary: Propylamycin is a next generation amino-glycoside antibiotic that has increased antibacterial potency compared to its parent compound and reduced ototoxicity. However, it is inactivated by a specific enzyme, leading researchers to study various derivatives in order to overcome this issue.
ACS INFECTIOUS DISEASES
(2021)
Meeting Abstract
Chemistry, Multidisciplinary
Vikram Sarpe, Amr Sonousi, Jonathan Quirke, Parasuraman Rajasekaran, Andrea Vasella, Erik Bottger, David Crich
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Meeting Abstract
Chemistry, Multidisciplinary
Santanu Jana, Vikram Sarpe, Suvarn Kulkarni
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Biochemistry & Molecular Biology
Vikram A. Sarpe, Michael G. Pirrone, Klara Haldimann, Sven N. Hobbie, Andrea Vasella, David Crich