Tetrahedron Letters p. 4045 - 4048 (1989)
Update date:2022-08-11
Topics:
Berube, Gervais
Fallis, Alex G.
A general intramolecular Diels-Alder:anionic oxy-Cope strategy for the synthesis of tricyclic skeletons and its application to the preparation of the gascardic acid precursor 12 is described.In situ generation of the appropriate cyclopentadiene 5 by isomerization (Et3N) afforded the <4+2> adduct directly or with EtAlCl2 as catalyst.The requisite potassium salt of the 1,5 diene 10 rearranged at 67 deg C to the fused ring ketone 11.Selecvtive allylic oxidation and reduction provided 12.
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