38301-74-5Relevant articles and documents
Regioselective palladium-catalyzed alkylation of allylic halides with benzylic Grignard reagents. Two-step synthesis of abietane terpenes and tetracyclic polyprenoid compounds
Rosales, Viale,Zambrano, Jorge L.,Demuth, Martin
, p. 1167 - 1170 (2002)
A highly regioselective palladium-catalyzed α-alkylation of allylic bromides 1a,c-e and chloride 1b with substituted and unsubstituted benzylic Grignard reagents is reported. The resulting alltrans polyenehomobenzene derivatives were obtained in excellent yields and regioselectivity. These products were easily converted to abietane-type diterpenes (10-12) and tetracyclic polyprenoid compounds (13, 14) through a Lewis acid-promoted cascade polyene cyclization reaction.
Design, synthesis and anthelmintic activity of 7-keto-sempervirol analogues
Crusco, Alessandra,Bordoni, Cinzia,Chakroborty, Anand,Whatley, Kezia C.L.,Whiteland, Helen,Westwell, Andrew D.,Hoffmann, Karl F.
supporting information, p. 87 - 100 (2018/05/07)
The plant-derived, diterpenoid 7-keto-sempervirol was recently reported to display moderate activity against larval stages of Schistosoma mansoni (IC50 = 19.1 μM) and Fasciola hepatica (IC50 = 17.7 μM), two related parasitic blood and liver flukes responsible for the neglected tropical diseases schistosomiasis and fascioliasis, respectively. Here, we aimed to increase the potency of 7-keto-sempervirol by total synthesis of 30 structural analogues. Subsequent screening of these new diterpenoids against juvenile and adult lifecycle stages of both parasites as well as the human HepG2 liver cell line and the bovine MDBK kidney cell line revealed structure-activity relationship trends. The most active analogue, 7d, displayed improved dual anthelmintic activity over 7-keto-sempervirol (IC50 ≈ 6 μM for larval blood flukes; IC50 ≈ 3 μM for juvenile liver flukes) and moderate selectivity (SI ≈ 4–5 for blood flukes, 8–13 for liver flukes compared to HepG2 and MDBK cells, respectively). Phenotypic studies using scanning electron microscopy revealed substantial tegumental alterations in both helminth species, supporting the hypothesis that the parasite surface is one of the main targets of this family of molecules. Further modifications of 7d could lead to greater potency and selectivity metrics resulting in a new class of broad-spectrum anthelmintic.
Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation
Youn, So Won,Pastine, Stefan J.,Sames, Dalibor
, p. 581 - 584 (2007/10/03)
(Matrix presented) We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).
