Journal of Organic Chemistry p. 4111 - 4117 (1980)
Update date:2022-08-05
Topics:
Pirkle, William H.
Adams, Paul E.
Enantiomerically pure bicyclic lactones 1-3 and tricyclic lactones 4 and 5 have been prepared by either of two procedures, each hinging upon the liquid chromatographic seperation of rationally selected diastereomeric derivatives.After seperation, the diastereomers are converted by a simple high-yield reaction sequence to the enantiomeric multiring lactones, none of which has been previously reported in optically active form. The relative strengths and weaknesses of each approach are discussed.Lactones 4 and 5 were α-methylated, these derivatives being suitable for the determination of enantiomeric purity and absolute configuration using the chiral solvating agent (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol.
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