218444-35-0Relevant academic research and scientific papers
Expeditious synthesis of the aromatic spiroketal skeleton using hetero-Diels-Alder cycloaddition
Zhou, Guanglian,Zheng, Deping,Da, Shijun,Xie, Zhixiang,Li, Ying
, p. 3349 - 3352 (2006)
The hetero-Diels-Alder reactions of enolic ethers generated from methylenation of various esters are described, which allow for the rapid synthesis of various substituted [6,6] aromatic spiroketal skeletons.
Benzofuran derivatives as anticancer inhibitors of mTOR signaling
Salomé, Christophe,Ribeiro, Nigel,Chavagnan, Thierry,Thuaud, Frédéric,Serova, Maria,De Gramont, Armand,Faivre, Sandrine,Raymond, Eric,Désaubry, Laurent
supporting information, p. 181 - 191 (2014/06/09)
A series of 32 derivatives and isosteres of the mTOR inhibitor 2 were synthesized and compared for their cytotoxicity in radioresistant SQ20B cancer cell line. Several of these compounds, in particular 30b, were significantly more cytotoxic than 2. Importantly, 30b was shown to block both mTORC1 and Akt signaling, suggesting insensitivity to the resistance associated to Akt overactivation observed with rapamycin derivatives currently used in clinic.
An approach to benzannelated [5,6]-spiroketals
Bray, Christopher D.
body text, p. 2500 - 2502 (2009/04/11)
Heating a variety of 2-hydroxybenzyl acetates bearing a range functional groups on the 4- or 5-position of the aromatic ring at 100°C in neat γ-methylene-γ-butyrolactone (1.0 M) for 20 hours gives a series of benzannelated [5,6]-spiroketals in 75-89% yiel
An efficient synthesis of highly functionalized [5,6] aromatic spiroketals by hetero-diels-alder reaction
Zhou, Guanglian,Zhu, Jianrong,Xie, Zhixiang,Li, Ying
supporting information; experimental part, p. 721 - 724 (2009/04/07)
A hetero-Diels-Alder reaction of vinyl sulfoxides with o-quinone methides precursor constructs highly functionalized [5,6] aromatic spiroketal skeletons in moderate to good yields with high regioselectivity. The two functional groups (ketone and olefin) c
Total synthesis of moracin C
McAllister, Graeme D.,Hartley, Richard C.,Dawson, Michael J.,Knaggs, Andrew R.
, p. 3453 - 3457 (2007/10/03)
Moracin C has been synthesised by the most efficient route to date (10 steps and 12% overall yield). The relatively unexplored acid-induced, intramolecular migration of an acyl group from an ortho phenolic hydroxy to a benzylic hydroxy is used to synthesise o-hydroxybenzylphosphonium salts containing ester groups. The phosphonium salts are coupled with 3,5-dimethoxybenzoic acid. Intramolecular Wittig reaction then gives 2-arylbenzo[b]furans, bearing the key 1′,3′,5′ substitution pattern on the aryl ring. This discovery provides a concise route to polyphenolic benzo[b]furans that we expect to be of general utility.
