Total synthesis of (±)-dihydroactinidiolide using selenium-stabilized carbenium ion
MJ Dabdoub, CC Silveira, EJ Lenardão, PG Guerrero…
Index: Dabdoub, Miguel J.; Silveira, Claudio C.; Lenardao, Eder J.; Guerrero Jr., Palimecio G.; Viana, Luiz H.; Kawasoko, Cristiane Y.; Baroni, Adriano C.M. Tetrahedron Letters, 2009 , vol. 50, # 40 p. 5569 - 5571
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Citation Number: 7
Abstract
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 α-chloro-α- phenylseleno ethyl acetate 14, affording the key intermediate, α-phenylseleno-γ-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1.
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