Syntheses of both diastereoisomers of 2,8-dioxabicyclo[3.2.1]octane derivatives: Degradation products of Daphniphyllum alkaloids

Article abstract of DOI:10.1246/cl.1999.1095

Both diastereoisomers of 1,4-dimethyl-2,8-dioxabicyclo[3.2.1]octane-4-caboxylic acid ester (3, 4) and the 4-hydroxy methyl analogues (5, 6) were synthesised from ethyl acetoacetate and diethyl malonate respectively. The key step of these process involved intramolecular cyclisation using palladium chloride as catalyst.