We have achieved the synthesis of 1-aryl-2-substituted 4-oxoquinoline and 4-oxo-1,8-naphthyridine derivatives, which cannot be synthesized by known methods, via two useful synthons, 2-formyl-4-oxoquinoline and 2-methylsulfonyl-4-oxo-1,8-naphthyridine. We also succeeded in the synthesis of 1-aryl-3-fluoro-4-oxoquinoline by fluorocyclization of N-arylenaminone with Selectfluor ® and potassium carbonate in DMF in a one-pot procedure. To the best of our knowledge, this is the first synthesis of 3-fluoro-4-oxoquinoline derivatives. We confirmed that these protocols were mutually applicable to the synthesis of 4-oxoquinoline and 4-oxo-1,8-naphthyridine derivatives.

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A New Synthetic Strategy for 2-Deoxy-D-ribose via Palladium(II)-Catalyzed Cyclization of Aldehyde. -The total synthesis of 2-deoxy-D-ribose (VIII) is achieved in 12 steps from L-(-)malic acid (I) via an unstable hemiacetal. The key step consists of the Pd(II)-catalyzed cyclization of aldehyde (II) and affords the cyclized product (IV) as an inseparable mixture of diastereomers. Oxidation of the diastereomers followed by reduction of the resulting aldehydes provide the corresponding primary alcohols which are deprotected to furnish the target compound (VIII). -(MIYAZAWA*, M.; AWASAGUCHI, K.-I.; UOYA, I.; YOKOYAMA, H.; HIRAI, Y.; Heterocycles

L i p a s e -C a t a l y z e d A s y m m e t r i c D e a l k o x y l c a r b o n y l a t i o n o f s -S y m m e t r i c a l b -K e t o d i e s t e r s Abstract: Optically active 2,6-dimethylcyclohexanone-2-carboxylate was prepared by PLE-catalyzed dealkoxycarbonylation of s-symmetrical b-ketodiesters, which possess quarternary carbons at a-and a¢-positions. Moreover, (-)-podocarpic acid was prepared in a short sequence from 2,6-dimethylcyclohexanone-2-carboxylate.

Various 2‐substituted 4‐oxoquinoline and 4‐oxo‐1,8‐naphthyridine derivatives are prepared from the key intermediates (I) and (VIII), respectively.