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Three different approaches are described for the generation of derivatives of 2,3-dimethyiene-2,3-dihydropyrrole 2, which are reactive intermediates in Diels-Alder cycloaddition reactions; one of the intramolecular cycloadditions provides a new tricyclo[3.2.1.0*~7]octane compound 8.

Isotetronic acids are subunits of a number of natural products. They are of interest in agricultural and pharmaceutical research and are important synthetic intermediates. This paper describes the first highly diastereo-and enantioselective synthesis of isotetronic acids in 4 to 5 steps (de, ee b 98 %). Key steps in the reaction sequence are the diastereoselective aldol reaction of the 2-oxoesters 5 as their SAEP hydrazones (S)-6 with aldehydes, followed by base-promoted lactonization to the hydrazonolactones 8. Subsequent oxidative cleavage of the hydrazone moiety afforded the enantiomerically pure O-protected isotetronic acids (R)-/(S)-9.

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