Earlier structures suggested for the products of the reaction between the ester (V; R = C02Et) and formaldehyde have been revised. This ester and related compounds give tricyclic pyridones (IX; R = CO,Et, etc.) with ethyl a-formylbutyrate.The dihydroisoquinoline (XV) condenses with esters of acetonedicarboxylic acid to give unusual cyclisation products, tentatively formulated as (XVI; R1 = H or CO,Alk, R2 = Alk).
The diastereoisomers of the ketones (XXII) and (XXIII) have been synthesised stereospecifically and their configurations assigned. The isomers of ketone (XXIII) have been converted severally into (&)-2,3-dehydroemetine and ( f ) -2,3-dehydroisoemetine.
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