Abstract
Synthesis and Face-Selective Diels-Alder Reaction of Homodehydroisodicyclopentadiene Under alkaline conditions the mesylate 6c, obtained from the tetracyclic ketone 6b fragments into the enone 8a. The latter is transformed via alcohol 9 into the homodehydroisodicyclopentadiene 3 and via tosylhydrazone 8b into the triene 4. Cyclopentadiene 3 reacts with a series of non-acetylenic dienophiles from the sterically less hindered side to give the products 14-17. Acetylenic dienophiles yield the adducts 19–22 in a 1:1 ratio. The UV and PE spectra of triene 4 are discussed.
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