Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline.
[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.
Silva
Luiz F
LF
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
Siqueira
Fernanda A
FA
Pedrozo
Eliane C
EC
Vieira
Fabiana Y M
FY
Doriguetto
Antônio C
AC
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
D007189:Indans; D008744:Methylamines; D009281:Naphthalenes; C418119:indatraline; D006859:Hydrogen; D007455:Iodine