Methoxypyridines in the synthesis of Lycopodium alkaloids: total synthesis of (+/-)-lycoposerramine R.
A methoxypyridine serves as a masked pyridone in a concise synthesis of the Lycopodium alkaloid lycoposerramine R, which has been prepared for the first time. The key step of the synthesis is the use of an Eschenmoser Claisen rearrangement to forge a key quaternary carbon center.
Bisai
Vishnumaya
V
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Sarpong
Richmond
R
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D011725:Pyridines; D011728:Pyridones; D012717:Sesquiterpenes; C520065:lycopladine A; C551369:lycoposerramine R