Preparation and thermal rearrangement of 2-(tert-butyldimethylsiloxy)-5-methyl-6-exo-[(Z)-3-methyl-1-butenyl]-4-exo-vinylbicyclo [3.1. 0] hex-2-ene. A total synthesis of …
E Piers, GL Jung
文献索引：Piers, Edward; Jung, Grace L. Canadian Journal of Chemistry, 1987 , vol. 65, p. 1668 - 1675
A total synthesis of the marine sesquiterpenoid (±)-sinularene (1) is described. The alcohol 19 was converted via an 8-step sequence into the bicyclic enone 28. Conjugate addition of lithium divinylcuprate to the latter substance afforded mainly the ketone 30, which was transformed into the enol silyl ether 6. Thermolysis (220° C, 4.5 h) of 6 provided cleanly the bicyclic triene 7, which, in two steps, was converted into the tricyclic olefinic ketone 34. ...
