1024598-08-0Relevant academic research and scientific papers
Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols via an Intramolecular Friedel?Crafts-Type 1,4-Addition: Access to Cannabidiol Analogues
Bryant, Laura A.,Cobb, Alexander J. A.,Johnston, Callum D.,Lees, Nicholas R.,Shankland, Kenneth,Straker, Hannah E.
supporting information, p. 4067 - 4074 (2021/07/20)
The organocatalytic transformation of resorcinols is extremely rare. In this article, we report a highly enantioselective, organocatalytic intramolecular cyclization of these systems by a Friedel–Crafts-type 1,4-addition using a J?rgensen-Hayashi-like organocatalyst with a large silyl protecting group, and show that heat improves reaction yield with virtually no detriment to enantioselectivity. A variety of bicyclic resorcinols were obtained with excellent enantioselectivities (up to 94%). To show the utility of these constructs, and as part of a wider project involving the synthesis of cannabinoid-like compounds, the resorcinol formed was used to generate both ‘normal’ and ‘abnormal’ cannabidiol (CBD) derivatives which were shown to have anticonvulsant activity. (Figure presented.).
Hg(OTf)2-catalyzed arylene cyclization
Namba, Kosuke,Yamamoto, Hirofumi,Sasaki, Ikuo,Mori, Kumiko,Imagawa, Hiroshi,Nishizawa, Muaio
supporting information; experimental part, p. 1767 - 1770 (2009/04/12)
Novel Hg(OTf)2-catalyzed arylene cyclization was achieved with highly efficient catalytic turnover (up to 200 times). The reaction takes place via protonation of allylic hydroxyl group by in situ formed TfOH of an organomercurlc intermediate to
