Article
Chemistry, Organic
Yang Liu, Ziyang Zhao, Chao Hu, Chuanfang Zhao, Jun Liu, Yuguo Du
Summary: An efficient stereoselective synthesis of brevipolide M was achieved in 13 linear steps with an overall yield of 17.8% based on a chiron approach. The key steps involved a tandem Wittig olefination-tetrahydrofuran cyclization and sequential ring-closing metathesis (RCM)-double-bond migration in one-pot processes.
Article
Chemistry, Organic
Kapil Sharma, Naresh Surineni, Sayani Das, Shivajirao L. Gholap
Summary: A concise and divergent chiron approach starting from d-ribose is reported for the first total synthesis of (+)-pseudonocardide A, (+)-pseudonocardide C, and an epimer of ent-pseudonocardide D. The synthesis features a highly Z-selective Wittig olefination, one-pot formation of gamma-butyrolactone and gamma-butenolide through [1,4] O-to-O silyl migration followed by lactonization and an intramolecular oxa-Michael reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Long Min, Li-Ping Zhong, Chuang-Chuang Li
Summary: Steroids continue to play a significant role in organic chemistry, medicinal chemistry, and drug discovery. However, the synthesis of unusual rearranged steroids, particularly abeo-steroids with a medium-sized ring, remains a challenge. This Account summarizes the laboratory's efforts in the total synthesis of abeo-steroids using cycloaddition strategies, highlighting the efficiency and versatility of each strategy in constructing structurally complex abeo-steroid cores. The findings provide valuable insights for advancing the total synthesis of abeo- and related steroids.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
K. C. Nicolaou, Ruocheng Yu, Zhaoyong Lu, G. Fernando Alvarez
Summary: Researchers have successfully synthesized a complex natural tropolonoid compound, gukulenin B, which is a challenging target for synthesis. They used a series of site-selective aromatic C-H bond functionalizations and C-C bond formations to successfully construct the tropolone nucleus. This study is of great significance for further synthesis and biological research, and provides new insights for the development of tropolone functionalization methods.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Deepak Saini, Praveen Kumar, Rodney A. Fernandes
Summary: A concise stereoselective total synthesis of two diastereomeric obolactones and 7 ',8 '-dihydroobolactones was achieved, establishing the structure and absolute configuration of these compounds for the first time.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Si-Qing Wang, Wei-Yi Qi, Xue-Song Yin, Bing-Feng Shi
Summary: This paper presents a concise formal total synthesis of (+/-)-7-deoxycylindrospermopsin in 14 steps from commercially available 4-methoxypyridine, with key steps including the elaboration of densely functionalized piperidine, Sonogashira coupling to attach the pyrimidine moiety, and intramolecular conjugate addition of guanidine with alkyne to form the C ring. The synthesis of its 8-epi isomer was also achieved following the same synthetic strategy.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Jinzheng Wang, Du'an Lin, Ming Liu, Han Liu, Pilar Blasco, Zhenquan Sun, Yan Chu Cheung, Sheng Chen, Xuechen Li
Summary: By streamlining solution phase-solid phase synthesis and chemical ligation-mediated peptide cyclization, the total synthesis of mannopeptimycin beta was achieved. Mannoeloptimycin beta, a cyclic glycopeptide, exhibits antibacterial activity against antibiotic-resistant Gram-positive pathogens.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Bei Wei, Peng Cheng, Liansuo Zu
Summary: This article reported the concise asymmetric total synthesis of gilbertine alkaloid from methyl jasmonate, using a cyclopentanone-based approach for the rapid assembly of the hydrocarbazole natural product.
Article
Chemistry, Organic
Scherin Fayad, Ardalan Jafari, Soeren M. M. Schuler, Michael Kurz, Oliver Plettenburg, Peter E. Hammann, Armin Bauer, Gerrit Juerjens, Christoph Poeverlein
Summary: The GE81112 series, consisting of three naturally occurring tetrapeptides and synthetic derivatives, is evaluated as a potential lead structure for the development of a new antibacterial drug. A second-generation synthesis of GE81112A is reported, which improves the stereoselectivity of the fi-hydroxy histidine intermediate synthesis and provides a stereoselective approach towards both orthogonally protected cis and trans-3-hydroxy pipecolic acid.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Katerina M. Korch, Donald A. Watson
Summary: The synthesis of the natural product impatien A was achieved using an aza-Heck cyclization to construct the complex spirocyclic ring system, showcasing an efficient synthetic method. Through high-throughput experimentation, a new ligand was identified to enable the key cyclization reaction, ultimately allowing impatien A to be synthesized in seven steps from known compounds.
Article
Chemistry, Organic
Minami Odagi, Taisei Matoba, Kazuo Nagasawa
Summary: In this paper, we describe the enantioselective total syntheses of cepharatines A-D, which are members of the hasubanan alkaloid family and feature an unusual tetracyclic skeleton including an azabicyclo[3.3.1]nonane motif. The key reaction involves a regio-divergent oxidative phenolic coupling reaction that efficiently affords the tricyclic core structure of hasubanan with different substitution patterns on the A-ring, including the all-carbon quaternary stereogenic center at C13, in a single step. Furthermore, the characteristic tetracyclic azabicyclo[3.3.1]nonane motif is constructed via a bioinspired cascade reaction involving the retro-aza-Michael reaction/hemiaminal formation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
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)
Article
Chemistry, Multidisciplinary
Leiyang Bai, Yinhao Ma, Xuefeng Jiang
Summary: Through a one-step catalytic operation, this study successfully designed a synthetic pathway for the total synthesis of isocalycanthine and its derivatives, which possess novel structures and alkaloid activities in dimeric cyclotryptamine alkaloids.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
R. A. Kovalevsky, A. S. Kucherenko, S. G. Zlotin
Summary: A practical asymmetric synthesis method of (S)-forphenicinol, the active ingredient of immunomodulator and anticancer drug Forfenimex (R), from commercially available 2-hydroxy-dimethylterephthalate has been developed. The key steps of the synthesis involve a stereogenic-center-forming enantioselective organocatalytic Mannich reaction and oxidative transformation of the gamma-pyrone fragment, resulting in a significantly higher total yield compared to known methods.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jiaxin Xie, Xin Liu, Nan Zhang, Shinyoung Choi, Guangbin Dong
Summary: The total synthesis of phainanoid A was achieved using a bidirectional synthetic strategy, which featured two highly diastereoselective transformations mediated by transition metals. The strategic use of ketones in key transformations allowed for rapid growth of molecular complexity, paving the way for efficient preparations of complex and biologically significant DTTs.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
