Conversion of leucomycin-A3 antibiotic into novel triazole analogues via regio- and diastereoselective SN1′ substitution with allylic rearrangement and 1,3-dipolar cycloaddition of CuAAC type
作者： Joanna Domagalska , Krystian Pyta , Piotr Przybylski
DOI: 10.1016/J.TETLET.2016.02.113
关键词: Acetal 、 Rate-determining step 、 Allylic rearrangement 、 1,3-Dipolar cycloaddition 、 Stereochemistry 、 Substituent 、 Chemistry 、 Nucleophilic substitution 、 Alkyne 、 Leaving group 、 Organic chemistry 、 Biochemistry 、 Drug discovery
摘要: Abstract In view of the complicated chemistry josamycin’s (leucomycin-A3) acetal functional groups, reduction aldehyde followed by nucleophilic substitution dienol system in aglycone yielded novel products having an alkyne group attached at C(13) carbon atom. Detailed 1H–1H NOESY and 1H–13C HMBC investigations together with DFT calculations indicated C(13S) configuration within structures alkyne-functionalized leucomycins. Analysis relationship between rate concentration revealed unimolecular mechanism protonation leaving as determining step. Further conversion substituent on using CuAAC reaction provided access to heterocyclic leucomycin analogues bearing substituted 1,2,3-triazole rings.
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