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

โœ Scribed by Paulo H.G. Zarbin; Alfredo R.M. de Oliveira; Carlos E. Delay

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
230 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 b-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-1,8-dihydroxy-5-nonanones 9 and 9a in four steps, and a subsequent stereoselective spiroketalization, in acidic media, afforded a Z:E mixture (1:2) of compounds 1 and 1a.

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## Synthesis of a mixture of (2S,5R)-and (2S,5S)-2-methyl-l,6-dioxaspiro[4.5]decane, the odor bouquet minor components of Paravespula vulgaris(L.), from L-sorbose \*