Science of Synthesis

Gandon, V.; Thorimbert, S.; Malacria, M., Science of Synthesis, (2009) 46, 219.

The catalytic palladium-catalyzed carbometalation of 1,6-enynes may lead to cyclic 1,3-dienes and 1,4-dienes as well as other cycloadducts. For example, in a productive approach, 1,6-enynes ‌159‌ give rise to vinylcyclopentenes ‌161‌ (‌Scheme 56‌) when a palladium(II) complex ‌160‌ ( R5 = Me, CH2CF3) associated with tri-2-tolyl phosphite and dimethyl acety­lenedicarboxylate is employed.[‌148‌–‌150‌] This type of reaction can be extended to the preparations of bicyclic analogues,[‌150‌,‌151‌] which may act as good precursors of more complex molecules as, for example, in the synthesis of roseophilin, a compound that exhibits antitumor activity.

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