Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids.
A concise enantioselective approach to the tetracyclic core of the magellanine-type Lycopodium alkaloids is reported. Key to this approach is the use of the Hajos-Parrish reaction to set a challenging quaternary stereocenter, thereby guiding the stereoselectivity for the remainder of the synthesis, as well as the use of a palladium-mediated direct pyridine functionalization reaction to forge the tetracyclic core.
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Rebecca A
RA
Murphy
Richmond
R
Sarpong
D000470:Alkaloids / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D011725:Pyridines; D010165:Palladium; C471075:magellanine; C023666:pyridine