51224-51-2Relevant academic research and scientific papers
Synthesis of two naturally occurring 3-methyl-2,5-dihydro-1-benzoxepin carboxylic acids
Yamaguchi, Seiji,Tsuchida, Nao,Miyazawa, Masahiro,Hirai, Yoshiro
, p. 7505 - 7511 (2005)
Two naturally occurring 3-methyl-2,5-dihydro-1-benzoxepin carboxylic acids, 6-hydroxy-3-methyl-8-(phenylethyl)-2,5-dihydro-1-benzoxepin-9-carboxylic acid (radulanin E) (1) and 9-hydroxy-3-methyl-2,5-dihydro-1-benzoxepin-7-carboxylic acid (2), were synthes
Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine
Chen, Peng,Bao, Xu,Zhang, Le-Fen,Ding, Ming,Han, Xiao-Jie,Li, Jing,Zhang, Guo-Biao,Tu, Yong-Qiang,Fan, Chun-An
supporting information; experimental part, p. 8161 - 8166 (2011/10/18)
Divergent route: A direct C-C bond-forming approach to the key aryl-substituted all-carbon quaternary stereogenic center present in bioactive hydrodibenzofuran alkaloids has been discovered. This approach involves an unprecedented organocatalytic enantioselective Michael addition of α-cyanoketones with acrylates (see scheme) and was used in a novel and divergent synthetic strategy for the title compounds in asymmetric fashion.
Synthesis and hydrolysis kinetics of 4-cyano-4-phenylpiperidine derivatives: A route to morphine analogs
Gervais,Anker,Chareire,Pacheco
, p. 241 - 248 (2007/10/05)
A description is given of a high-yield synthesis leading to various hydroxy-2 phenylacetonitriles and to various benzodihydro-2,3 furannones-2. The intermediary 12 benzylic mesylates give quantitatively the corresponding 11 chlorides by the action of hydrochlorate of triethylamine; this procedure constitutes a very rewarding and easy method for chlorinating the benzylic alcohols in two stages without isolating the intermediary. A proximate effect has been shown which makes possible the hydrolysis of certain phenylacetonitriles by dilute acetic acid. This hydrolysis becomes very rapid when these nitriles are distributed; the increase of the speed of the hydrolysis illustrates the gem dialkyle effect.
