49830-37-7Relevant articles and documents
Total syntheses of (±)-massadine and massadine chloride
Su, Shun,Seiple, Ian B.,Young, Ian S.,Baran, Phil S.
, p. 16490 - 16491 (2008)
The total syntheses of the complex pyrrole-imidazole alkaloids (±)-massadine and (±)-massadine chloride is described using a carefully orchestrated sequence of manipulations on highly polar and structurally complex intermediates. Key to the completion of this synthetic endeavor was the exploration of a unique and chemoselective method to oxidize unprotected guanidines under aqueous conditions in air. This oxidation has been optimized and applied to a selection of spirocyclic guanidines of varying complexity. Additionally, the 3,7-epi analogues of these interesting natural products have been synthesized and fully characterized. Copyright
Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia
Li, Qing-Hua,Li, Zhao-Feng,Tao, Jing,Li, Wan-Fang,Ren, Li-Qing,Li, Qian,Peng, Yun-Gui,Liu, Tang-Lin
supporting information, p. 8429 - 8433 (2019/10/14)
α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.
Design and Synthesis of Fsp3-Rich, Bis-Spirocyclic-Based Compound Libraries for Biological Screening
Stotani, Silvia,Lorenz, Christoph,Winkler, Matthias,Medda, Federico,Picazo, Edwige,Ortega Martinez, Raquel,Karawajczyk, Anna,Sanchez-Quesada, Jorge,Giordanetto, Fabrizio
supporting information, p. 330 - 336 (2016/07/06)
The exploration of innovative chemical space is a critical step in the early phases of drug discovery. Bis-spirocyclic frameworks occur in natural products and other biologically relevant metabolites and show attractive features, such as molecular compactness, structural complexity, and three-dimensional character. A concise approach to the synthesis of bis-spirocyclic-based compound libraries starting from readily available commercial reagents and robust chemical transformations has been developed. A number of novel bis-spirocyclic scaffold examples, as implemented in the European Lead Factory project, is presented.