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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, Organic
Xin-Ting Liang, Bao-Chuan Sun, Chang Liu, Yuan-He Li, Nan Zhang, Qian-Qian Xu, Zhong-Chao Zhang, Yi-Xin Han, Jia-Hua Chen, Zhen Yang
Summary: A concise and diastereoselective method has been developed for the construction of the key ring system of spirochensilide A, paving the way for the first asymmetric total synthesis of (-)-spirochensilide A.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Ingrid K. Wilt, Adrian R. Demeritte, Weiwei Wang, William M. Wuest
Summary: Synthetic investigations of natural products have played an important role in developing novel antibacterial small molecules. The total synthesis of 1-hydroxyboivinianin A and its enantiomer with a six-step sequence yielded 42% overall. Both enantiomers showed negligible antibacterial activity against a panel of gram-positive and negative bacteria, as well as minimal antifungal activity against phytopathogens.
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.
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Chemistry, Multidisciplinary
Benedetta Bassetti, Roberto Ballini, Pietro Allegrini, Giancarlo Aldini, Alessandro Palmieri
Summary: This study presents a new practical and efficient multistep synthesis method for the production of 1- and 2-hydroxycannabidiol metabolites. The target metabolites were successfully produced with good overall yields, and the reactions are easily feasible.
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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
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
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
Yun-Peng Zou, Zheng-Lin Lai, Meng-Wei Zhang, Jianzhao Peng, Shuai Ning, Chuang-Chuang Li
Summary: The first total synthesis of (+/-)- and (-)-daphnilloninB, a daphnicyclidin-type alkaloid with a novel hexa-cyclic core, was achieved through a series of chemical reactions. The B/C/D ring system was efficiently constructed using a mild intramolecular cycloaddition and a GrubbsII catalyst-catalyzed radical cyclization. The E/F fused ring system was synthesized via a diastereo-selective intramolecular Pauson-Khand reaction. The challenging hexa-cyclic core was reassembled from a hexa-cyclic framework found in calyciphylline A-type Daphniphyllum alkaloids through a unique Wagner-Meerwein rearrangement.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(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
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
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, Multidisciplinary
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)