Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones. First total synthesis of both enantiomers of pipermethystine.
[reaction: see text]. A novel enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones using a ring closing metathesis and a lipase-mediated kinetic resolution as key steps is described and applied to the first synthesis of both enantiomers of pipermethystine.
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Emory University, Department of Chemistry, 1515 Pierce Drive, Atlanta, Georgia 30322, USA.
Alcudia
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Liebeskind
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D000470:Alkaloids / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical; D003500:Cyclization; D020901:Kava / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D011728:Pyridones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D011728:Pyridones; C448623:pipermethystine