2-(pent-4-ynyl)norbornadienes undergo an intramolecular [2+2+2] cycloaddition in the presence of (nbd)RuCl2(PPh3)2 as a catalyst affording annelated deltacyclenes in good to excellent yields. The usefulness of the reaction is illustrated by the straighforward conversion of pentacyclene 2a into the angularly fused triquinane 19.
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Tenaglia et al. (2007) studied this question.
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