Artículos de revistas
Total synthesis of (+/-)-dihydroactinidiolide using selenium-stabilized carbenium ion
Fecha
2009Registro en:
TETRAHEDRON LETTERS, v.50, n.40, p.5569-5571, 2009
0040-4039
10.1016/j.tetlet.2009.07.067
Autor
DABDOUB, Miguel J.
SILVEIRA, Claudio C.
LENARDAO, Eder J.
GUERRERO JR., Palimecio G.
VIANA, Luiz H.
KAWASOKO, Cristiane Y.
BARONI, Adriano C. M.
Institución
Resumen
A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and alpha-chloro-alpha-phenylseleno ethyl acetate 14, affording the key intermediate, alpha-phenylseleno-gamma-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1. (C) 2009 Elsevier Ltd. All rights reserved.