Synthesis Club

Diagram of clionastatin B, a chemical compound, showing its molecular structure with various chlorine (Cl) and methyl (Me) groups attached. The diagram emphasizes the arrangement of atoms and bonds in the compound, important for understanding its chemical properties and potential applications.

Asymmetric Total Synthesis of Clionastatins A and B

W. Ju, X. Wang, H. Tian, J. Gui J. Am. Chem. Soc. 2021, 143, 13016–13021.

Chemical structure of lingzhiol, depicting its molecular layout with functional groups like hydroxyl (-OH) attached to a carbon framework. This compound is relevant in the context of research on medicinal properties and synthesis techniques.

A General Entry to Ganoderma Meroterpenoids: Synthesis of Applanatumol E, H, and I, Lingzhilactone B, Meroapplanin B, and Lingzhiol

A. Rode, N. Müller, O. Kováč, K. Wurst, T. Magauer Org. Lett. 2024, 26, 9017–9021.

The image depicts the molecular structure of nidutrepenoid B, showcasing various atoms and bonds, including hydroxyl (OH) and methyl (Me) groups. The structure is presented in a scientific diagram format, emphasizing connectivity between atoms.

Total Synthesis of the Hexacyclic Sesterterpenoid Niduterpenoid B via Structural Reorganization Strategy

Xue, Y.; Hou, S.-H.; Zhang, X.; Zhang, F.-M.; Zhang, X.-M.; Tu, Y.-Q. J. Am. Chem. Soc. 2024, 146, 254454–25450.

The image shows the chemical structure of borolithochrome G, featuring various interconnected rings and functional groups, including hydroxyl and boron elements. The structure is visually represented with labels indicating its name for identification in a scientific context.

Total Syntheses of Borolithochromes A, D and G

K. Kirita, H. Matsumoto, G. Endo, S. Hosokawa Angew. Chem. Int. Ed. 2024, 63, e202400586

The image depicts the chemical structure of pepluacetal, featuring a complex arrangement of carbon (C), oxygen (O), and hydrogen (H) atoms, along with various methyl (Me) groups attached to the main structure. The molecular diagram shows connections and bonds indicative of its chemical properties.

Total Synthesis of the Euphorbia Diterpenoid Pepluacetal

Liu, M.; Wu, C.; Xie, X.; Li, H.; She, X. Angew. Chem. Int. Ed. 2024, 68, e202400943.

Chemical structure of pactamycin, featuring various functional groups represented by molecular formulas and bonds. The image illustrates the intricate arrangement of atoms, showcasing the compound's complexity relevant to drug research and synthesis.

Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic

Justin T. Malinowki, Robert J. Sharpe, Jeffrey S. Johnson Science, 2013, 340, 180–182.

Chemical structure of complanadine A, featuring multiple nitrogen atoms and a variety of connected carbon rings. The structure includes several methyl (Me) groups and highlights key bonds within the molecule.

Concise Total Synthesis of Complanadine A

D. Ma, B. S. Martin, K. S. Gallagher, T. Saito, and M. Dai Synthesis 2024, 56, 107–117; J. Am. Chem. Soc. 2021, 143, 16383–16387.

Chemical structure of tetrodotoxin, a potent neurotoxin. The image includes various hydroxyl (OH) groups and a nitrogen (N) atom, indicating its complex molecular configuration. The substance is known for its toxicity and is often associated with certain marine animals.

A concise synthesis of tetrodotoxin

Konrad, D.B., Rühmann, K., Ando, H., Hetzler, B.E., Strassner, N., Houk, K.N., Matsuura, B.S., Trauner, D. Science, 2022, 377, 411–415.

The image displays the molecular structure of (±)-daphenylline, highlighting its various atoms and bonds. Key elements include nitrogen (N) and carbon (C) atoms, along with hydrogen (H) and methyl (Me) groups. This structure is relevant in the context of chemistry and pharmacology.

Navigating Excess Complexity: Total Synthesis of Daphenylline

Wright, BB. A., Regni, A., Chaisan, N., Sarpong, R. J. Am. Chem. Soc. 2024, 146, 1813–1818.

The image displays the molecular structure of (–)-strychnine, a toxic alkaloid. It includes rings and nitrogen atoms, with specific bonds indicated. The compound is labeled clearly below its structure.

Asymmetric Total Syntheses of (–)- and (+)-Strychnine and the Wieland–Gumlich Aldehyde

Steven D. Knight, Larry E. Overman, Garry Pairaudeau J. Am. Chem. Soc. 1995, 117, 5776–5788.

The image depicts the chemical structure of aleutianamine, featuring various atoms including nitrogen (N), oxygen (O), sulfur (S), and bromine (Br). The structure is presented with labels, indicating the presence of trifluoroacetic acid (TFA) and specific functional groups within the compound.

Total Synthesis of Aleutianamine

Hao Yu, Zachary P. Sercel, Samir P. Rezgui, Jonathan Farhi, Scott C. Virgil, Brian M. Stoltz J. Am. Chem. Soc. 2023, 145, 25533–25537.

Chemical structure of metapanine, showing various functional groups including methoxy and hydroxyl. The illustration emphasizes its molecular composition for educational or informational purposes.

Total Synthesis of Metaphanine and Oxoepistephamiersine

Ya-Kui Sun, Jin-Bao Qiao, Yu-Meng Xin, Qin Zhou, Zhi-Hua Ma, Hui Shao, Yu-Ming Zhao Angew. Chem. Int. Ed. 2023, 62, e202310917.

Chemical structure of illisimonin A, featuring multiple hydroxyl (OH) groups and methyl (Me) groups, along with a complex ring structure. The diagram represents a significant compound in drug research, relevant to the synthesis strategies discussed on the accompanying webpage.

Asymmetric Total Synthesis of Illisimonin A

Etling, C., Tedesco, G., Di Marco, A., Kalesse, M. J. Am. Chem. Soc. 2023, 145, 7021–7029.

Structural diagram of (+)-ineleganolide, a chemical compound. The image highlights its molecular structure, including various functional groups and bonds. This compound is discussed in the context of its therapeutic potential in drug discovery.

A Convergent Total Synthesis of (+)-Ineleganolide

Gross, Benjamin M.; Han, Seo-Jung; Virgil, Scott C.;Stoltz, Brian M. J. Am. Chem. Soc. 2023, 145, 7763–7767.

Chemical structure of sacrolide A, featuring a complex arrangement of rings and functional groups including hydroxyl (--OH) and carbonyl (C=O) groups. The name "sacrolide A" is displayed below the structure.

Enantioselective total synthesis of sacrolide A

T. Mohri, Y. Ogura, R. Towada, S. Kuwahara Tetrahedrom Lett. 2017, 58, 4011-4013.

Chemical structure of (+)-strempeliopidine, featuring multiple rings and nitrogen atoms. The notation includes "Me" indicating methyl groups. This compound is part of research on potential therapeutic applications.

Total Synthesis of Strempeliopidine and Non-Natural Stereoisomers through a Convergent Petasis Borono–Mannich Reaction

Rand, A.W.; Gonzalez, K.J.; Reimann, C.E.; Virgil, S.C; Stoltz, B.M. J. Am. Chem. Soc. 2023, 145, 7278–7287.

Chemical structure of (−)-caulamidine A, featuring multiple nitrogen (N), chlorine (Cl), and methyl (Me) groups. The diagram highlights the connectivity and arrangement of atoms, essential for understanding its molecular formula and configuration.

Enantioselective Total Synthesis of (−)-Caulamidine A

Zhouyang Zhu and Thomas J. Maimone J. Am. Chem. Soc. 2023, 145, 14215–14220.

The image displays the chemical structure of (+)-waixenicin A, highlighting its molecular components, including various functional groups and carbon atoms arranged in a specific configuration. The structure exemplifies the complexity of organic compounds in scientific research.

Total Syntheses of (+)-Waixenicin A, (+)-9-Deacetoxy-14,15-deepoxyxeniculin, and (−)-Xeniafaraunol A

Steinborn, C., Huber, T., Lichtenegger, J., Plangger, I., Wurst, K., & Magauer, T. J. Am. Chem. Soc. 2023, 145, 11811–11817.

Chemical structure of eupalinilide E, featuring various functional groups including hydroxyl and methyl groups, illustrated with chemical bonds. The molecular formula is not provided, but the structure highlights key components relevant to its synthesis and potential biological activity.

Synthesis of Eupalinilide E, a Promoter of Human Hematopoietic Stem and Progenitor Cell Expansion

Johnson, T.C., Chin, M.R., Han, T., Shen, J.P., Rana, T., Siegel, D. J. Am. Chem. Soc. 2016, 138, 6068–6073

The image depicts the chemical structure of lycopodine, featuring various connected atoms and functional groups, including nitrogen (N), oxygen (O), and a methyl group (Me). The structure is represented in a simplified diagram format, with the name "lycopodine" labeled underneath.

Enantioselective Total Synthesis of Lycopodine

Hua Yang, Rich G. Carter and Lev N. Zakharov J. Am. Chem. Soc. 2008, 130, 9238–9239.

Chemical structure of (+)-hexacyclinol is presented, showcasing its molecular configuration with various functional groups and a series of carbon rings. The diagram includes symbols representing methyl (Me) groups and hydroxyl (OH) functional groups, highlighting its complex organic structure.

Total Synthesis and Structure Assignment of (+)-Hexacyclinol

Porco, J.A., Jr.; Su, S.; Lei, X.; Bardhan, S.; Rychnovsky, S.D. Angew. Chem. Int. Ed.  2006, 45, 5790 – 5792.

Chemical structure of vilmoraconitine, featuring various labeled atoms such as carbon (C), nitrogen (N), and oxygen (O). The structure includes multiple functional groups and is depicted in a simplistic diagram. The name "vilmoraconitine" is displayed beneath the structure.

Total Synthesis of Vilmoraconitine

Ji, J; Chen, J; Qin, S; Li, W; Zhao, J; Li, G; Song, H; Liu, X-Y; Qin, Y J. Am. Chem. Soc. 2023, 145, 3903–3908.

Structural diagram of daphgraciline, a chemical compound. The illustration includes labeled functional groups such as hydroxyl (OH), methoxy (O-Me), and carbonyl (CO2Me), highlighting its molecular features for research purposes.

Total Synthesis of Yuzurine-type Alkaloid Daphgraciline

Li, L.-X.; Min, L.; Yao, T.-B.; Ji, S.-X.; Qiao, C.; Tian, P.-L.; Sun, J.; Li, C.-C. J. Am. Chem. Soc. 2022, 144, 18823 – 18828.

Chemical structure of (+)-1-deoxylycorine, featuring interconnected rings, functional groups, and nitrogen atoms. Beneath the structure, the name "+(1)-deoxylycorine" is displayed.

The First Asymmetric Synthesis of a Lycorine Alkaloid. Total Synthesis of (+)-1-Deoxylycorine

A. G. Schultz, M. A. Holoboski, M. S. Smyth J. Am. Chem. Soc. 1993, 115, 7904–7905.

The image depicts the molecular structure of (−)-vinigrol, showing the arrangement of carbon and hydroxyl (OH) groups. Key features include two methyl groups (Me) and several hydroxyl groups connected to a complex carbon framework.

Scalable Total Synthesis of (–)-Vinigrol

Xuerong Yu, Lianghong Xiao, Zechun Wang, Tuoping Luo J. Am. Chem. Soc. 2019, 141, 3440–13443.

Alternative text: "Chemical structure of (+)-aureol, featuring a complex arrangement of rings and functional groups, including hydroxyl (OH) and methyl (Me) groups, representing its molecular composition relevant to medicinal research."

Highly Efficient Total Synthesis of the Marine Natural Products (+)-Avarone, (+)-Avarol, (−)-Neoavarone, (−)-Neoavarol and (+)-Aureol

J. Sakurai, T. Oguchi, K. Watanabe, H. Abe, S. Kanno, M. Ishikawa, and T. Katoh Chem. Eur. J. 2008, 14, 829 – 837.

Diagram comparing two structural representations of (+)-perseanol: a "road-kill" representation on the left, showing bonds and functional groups, and a "perspective" drawing on the right, emphasizing 3D orientation. Both illustrate the same chemical compound with annotations for clarity.

A 16-step synthesis of the isoryanodane diterpene (+)-perseanol

Han, A.; Tao, Y.; Resiman, S. E. Nature 2019, 573, 563–568.

The image displays molecular structures for two compounds: Microsphaeropsin B and Periconianone C, labeled accordingly. These chemical structures illustrate the arrangement of atoms and functional groups within each compound, essential for understanding their characteristics and potential applications in research.

The Furan Shuffling Hypothesis: A Biogenetic Proposal for Eremophilane Sesquiterpenoids

N. Lardon, R. Liffert, A. Linden, K. Gademann Angew. Chem. Int. Ed. 2019, 58, 7004–7007.

Chemical structure of salvinorin A, a compound derived from the Salvia divinorum plant, depicted with various functional groups and bonds. The structure includes rings, hydroxyl groups, and an acetoxy group, emphasizing its configuration and molecular connectivity.

Second-generation synthesis of salvinorin A

H. Hagiwara, Y. Suka, T. Nojima, T. Hoshi, T. Suzuki Tetrahedron 2009, 65, 4820–4825.

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