Tetrahedron Letters p. 783 - 786 (1996)
Update date:2022-07-30
Topics:
Harmata
Jones
Aldehyde 9 can be prepared from ethyl pyruvate in several steps. Treatment of 1 with various diene-containing Grignard reagents results in the formation of the corresponding allylic alcohol in good yield. Exposure of these alcohols to triflic anhydride results in the formation of 4+3 cycloadducts in good to excellent yields. Furan and simple butadiene trap the intermediate allylic cation efficiently in the formation of 5,7-fused ring systems. A tethered thiophene undergoes only intramolecular Friedel-Crafts alkylation.
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