Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes:: A diastereoselective total synthesis of (±)-indatraline

被引：79
|
作者：
Silva, Luiz F., Jr.
Siqueira, Fernanda A.
Pedrozo, Eliane C.
Vieira, Fabiana Y. M.
Doriguetto, Antonio C.
机构：
[1] Univ Sao Paulo, Inst Quim, BR-05513970 Sao Paulo, Brazil
[2] Univ Fed Alfenas, Dept Ciencias Exatas, BR-37130000 Alfenas, MG, Brazil
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 08期
关键词：
D O I：
10.1021/ol070027o
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：1433 / 1436
页数：4
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