Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 30, Issue 9, Pages 1970-1973Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201200295
Keywords
methylation; conformer; energy barrier; synthesis; perophoramidine
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Funding
- NSFC [20825207, 21002066, 21021001]
- PCSIRT [IRT0846]
- National Basic Research Program of China (973 program) [2010CB833200]
- National Science and Technology Major Project of China [2011ZX09401-304]
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An alternative N1-methylation strategy was reported in the late-stage of the total synthesis of (+)-perophoramidine. Preparation of (+)-perophoramidine was featured by an acid-catalyzed isomerization of amidine 5 to its C?N double bond tautomer 8, followed by two steps of N1-methylation with NaHMDS/MeOTf and oxidation with MnO2. In contrast, direct methylation of amidine 5 afforded the N23-methylation conformers 9a and 9b. Further oxidation of 9a and 9b led to N23-methylated perophoramidine.
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