Studies toward the synthesis of palhinine lycopodium alkaloids: a Morita-Baylis-Hillman/intramolecular Diels-Alder approach.
A synthetic route to the isotwistane core of palhinine lycopodium alkaloids is described. A Morita-Baylis-Hillman/intramolecular Diels-Alder (IMDA) strategy sets the vicinal all-carbon quaternary centers present in this family of natural products. The regioselectivity of the IMDA reaction is dictated by the conditions employed for silyl enol ether formation, with one set of conditions providing the core of cardionine and alternate conditions generating the desired isotwistane core of isopalhinine.
Department of Chemistry, 1102 Natural Sciences II, University of California , Irvine, California 92697-2025, United States.
Nicholas
N
Sizemore
Scott D
SD
Rychnovsky
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D061565:Cycloaddition Reaction; D032502:Lycopodium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; C553649:palhinine A