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2005
Bridged compounds
Q 0060
Synthesis of Bicyclo[4.n.1]alkanones. — Basic treatment of the β-keto esters (IIIa)
in formation of the bicycloalkanone (IV). Under similar conditions, the homo06- 077 results
logues (IIIb)-(IIIe) do not yield the desired bicycloalkanones but the fused furans (V).
The latter can be transformed into bicyclo[4.n.1]alkanones by flash vacuum thermolysis. In the presence of HCl, the fused furan (Va) undergoes rearrangement to the spirolactone (VII). The flash vacuum method can also be applied to prepare more complex
bridged ketones such as the tricyclic system (XVIII), a substructure found in the
ingenane family. — (MONTALT, J.; LINKER, F.; RATEL, F.; MIESCH*, M.; J. Org.
Chem. 69 (2004) 20, 6715-6721; Lab. Chim. Org. Synth., CNRS, Inst. Chim., Univ.
Louis Pasteur, F-67008 Strasbourg, Fr.; Eng.) — Jannicke
2005
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