title: Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline.
abstract: [reaction: see text] A new approach for the synthesis of (+/-)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.
authors: Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil. luizfsjr@iq.usp.br
authors: Luiz F
authors: LF
authors: Silva
authors: Fernanda A
authors: FA
authors: Siqueira
authors: Eliane C
authors: EC
authors: Pedrozo
authors: Fabiana Y M
authors: FY
authors: Vieira
authors: Antônio C
authors: AC
authors: Doriguetto
mesh_terms: D006859:Hydrogen / Q000737:chemistry*; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D008744:Methylamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D007189:Indans; D008744:Methylamines; D009281:Naphthalenes; C418119:indatraline; D006859:Hydrogen; D007455:Iodine