Tetrahedron letters

Diastereoselective route to (2R, 5S)-and (2S, 5S)-2-methyl-1, 6-dioxaspiro [4.5] decane, a pheromone component of the wasp Paravespula vulgaris

PHG Zarbin, ARM de Oliveira, CE Delay

Index: Zarbin, Paulo H. G.; De Oliveira, Alfredo R. M.; Delay, Carlos E. Tetrahedron Letters, 2003 , vol. 44, # 36 p. 6849 - 6851

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Citation Number: 14

Abstract

A diastereoselective approach to (2R, 5S)-and (2S, 5S)-2-methyl-1, 6-dioxaspiro [4.5] decane 1 and 1a is described. The route starts with an alkylation reaction among the cyclopentanone N, N-dimethylhydrazone 6 and the chiral iodides (R)-3 or (S)-3, derived from the enantiomers of ethyl β-hydroxybutyrate, controlling the estereocenter at C-2 of the molecules. The alkylated products 7 and 7a were easily transformed into the 1, 8-O-TBS-1 ...

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