33462-80-5Relevant articles and documents
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Badet,B.,Julia,M.
, p. 1101 - 1104 (1979)
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Synthesis of four novel natural product inspired scaffolds for drug discovery
Jenkins, Ian D.,Lacrampe, Fabienne,Ripper, Justin,Alcaraz, Lilian,Van Le, Phuc,Nikolakopoulos, George,De Leone, Priscila Almeida,White, Rodney H.,Quinn, Ronald J.
supporting information; experimental part, p. 1304 - 1313 (2009/07/04)
Inspired by the novel spiro structures of a number of bioactive natural products such as the histrionicotoxins, a series of novel spiro scaffolds have been designed and robust syntheses developed. The scaffolds are ready-to-use building blocks and can be easily prepared on a 5-20 g scale. They contain two amino groups (one Boc-protected) and have been designed for ease of conversion to a lead generation library, using either amide formation or reductive amination procedures. The synthesis of the 1,9-diazaspiro[5.5]undecane and 3,7-diazaspiro[5.6]dodecane ring systems was achieved using RCM as the key step. A simple workup procedure is reported for the removal of highly colored ruthenium residues. The synthesis of the 1,8-diazaspiro[4.5]decane scaffold has been achieved using a bromine-mediated 5-endo cyclization of the corresponding 4-aminobutene intermediate under acidic conditions. This is the first example of this type of cyclization to be reported. A novel mechanism involving a bromine transfer reaction from an initially formed bromonium ion to a neighboring nitrogen atom is suggested as the reason for the failure of this type of reaction under "normal" bromination conditions. An unusual rearrangement of a 1-acyl-1,9-diazaspiro[5.5]undecane to the corresponding 9-acyl-1,9-diazaspiro[5.5]undecane is reported.
Alkyl diaryl sulfonium salts
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, (2008/06/13)
Alkyl diaryl sulfonium salts, e.g., cyclopropyl diphenylsulfonium tetrafluoroborate, are useful as hypoglycemic agents.
