Abstract
An efficient synthesis of norbornene annulated cyclopentenones 5 and 18 starting from readily available tricyclodecadienone carboxylic acid 2a is described. Parent tricyclo[5.2.1.0 2,6]decadi-2(6),8-ene 5 , an hitherto unknown compound, has been obtained in good yield by subjecting bromide 7b to base induced elimination or by oxidative deselenylation of 7c . 5-Substituted analogues 18 are conveniently obtained from phenylselenide 3c by stereoselective conjugate cuprate addition followed by oxidative elimination of the seleno group. Dehydrobromination of epoxy bromide 21 affords norbornene-annulated cyclopentadienone 22 which immediately undergoes stereoselective 1,4-addition at the strained C 2–C 6 enone moiety to give 23 . These novel norbornene annulated cyclopentenones can be considered as the synthetic equivalent of 2-cyclopentynones.
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