132277-10-2Relevant academic research and scientific papers
Gram-Scale Robust Synthesis of 1-Chloro-2,3-dimethyl-4-phenylnaphthalene: A Promising Scaffold with Three Contiguous Reaction Positions
Moriguchi, Kento,Kono, Taro,Seko, Shinzo,Tanabe, Yoo
, p. 3811 - 3817 (2020)
A three-step reaction sequence for the gram-scale synthesis of 1-chloro-2,3-dimethyl-4-phenylnaphthalene was developed. (i) Stereoselective dichlorocarbene addition to methyl angelate afforded methyl (1 S*,3 S*)-2,2-dichloro-1,3-dimethylcyclopropane-1-carboxylate (78% yield, >98% purity, distillation). (ii) Addition reaction of two molar amounts of PhLi afforded (1 S*,3 S*)-2,2-dichloro-1,3-dimethylcyclopropyldiphenylmethanol (81% yield, >98% purity, recrystallization). (iii) Key SnCl 4-mediated benzannulation produced the desired product (83% yield, >98% purity, recrystallization) with three contiguous reaction sites. Five derivatization examples including benzylic reactions and cross-couplings at the pendant Cl-position are demonstrated. Some relevant distinctive benzannulations are also discussed.
A novel synthesis of α- and β-halonaphthalenes via regioselective ring cleavage of aryl(gem-dihalocyclopropyl)methanols and its application to total synthesis of lignan lactones, justicidin e and taiwanin c
Seko, Shinzo,Tanabe, Yoo,Suzukamo, Gohfu
, p. 6883 - 6886 (2007/10/02)
Acid treatment of two types of aryl(gem-dihalocyclopropyl)methanols (ADCM) 1 gave α- and β-halonaphthalenes in good yields with excellent selectivity. With the new method used as the key step, the two title natural lignan lactones were synthesized in seve
