Abstract
In view of the complicated chemistry of josamycin’s (leucomycin-A3) acetal functional groups, reduction of the aldehyde followed by nucleophilic substitution of josamycin’s dienol system in the aglycone yielded novel products having an alkyne group attached at the C(13) carbon atom. Detailed 1H–1H NOESY and 1H–13C HMBC investigations together with DFT calculations indicated the C(13S) configuration within the structures of alkyne-functionalized leucomycins. Analysis of the relationship between the rate of nucleophilic substitution and concentration revealed the unimolecular mechanism of the substitution with protonation of the leaving group as the rate determining step. Further conversion of the alkyne substituent on the aglycone using the CuAAC reaction provided access to novel heterocyclic leucomycin analogues bearing substituted 1,2,3-triazole rings.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
