Abstract
Catalytic reduction of 1-(p-methoxyphenyl)-3, 5-dimethyl-3-azabicyclo [3. 3. 1] nonane ⊿9, α-acetaldehyde (II) gave two epimeric saturated aldehydes (IIIa) and (IIIb). Both epimers were converted into the stereoisomeric hydrophenanthrene derivatives, VIa and VIb, respectively, by reduction with lithium aluminum hydride followed by cyclization with polyphospholic acid. The conformation of the stereoisomers was confirmed by determining the configuration of two epimeric alcohols (Va) and (Vb) from which these hydrophenanthrene compounds were derived. The A/B trans-fused isomer bears the common skeleton of the atisine-type alkaloids.
