Total synthesis of (+)-complanadine a using an iridium-catalyzed pyridine C-H functionalization
The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.
Fischer, Daniel F.,Sarpong, Richmond
scheme or table
p. 5926 - 5927
(2010/07/05)
Selective N-debenzylation of amides with p-TsOH
N-Benzylamides were debenzylated efficiently with 4 equiv. of p-TsOH in refluxing toluene. Good to quantitative yields of the desired primary amides were obtained within 2-4 h from a wide variety of N-2,4-dimethoxybenzylamides. N-4-Methoxylbenzyl amides and N-benzylamides were also debenzylated cleanly. In the case of N-2,4-dimethoxylbenzylamides, selective N-debenzylation was possible in the presence of N-Fmoc, N-t-BOC or N-trityl-protection. Protected amino acid amides survived these conditions without any detectable epimerization.
Chern, Ching-Yuh,Huang, Yu-Ping,Kan, Wai Ming
p. 1039 - 1041
(2007/10/03)
Synthesis of 6-Hydroxy-3,4,5,6-tetrahydro-2-pyridones and 3,4-Dihydro-2-pyridones by H2O2/DMSO Hydration of δ-Ketonitriles