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Synthesis of 3S-methylundec-1-ylbromide, a key synthon in the synthesis of (S,S,S)-diprionylacetate, from L-(-)-menthol
Authors:G. Yu. Ishmuratov  M. P. Yakovleva  V. A. Ganieva  R. Ya. Kharisov  R. R. Gazetdinov  A. M. Abulkaramova  G. A. Tolstikov
Affiliation:(1) Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054 Ufa, pr. Oktyabrya, 71;(2) Birsk State Social-Pedagogical Academy, 452320, RF, Birsk, ul. Internatsional’naya, 10
Abstract:Three new approaches to the synthesis of 1-bromo-3S-methylundecane, a key synthon in the synthesis of (S,S,S)-diprionylacetate, a sex pheromone of pine sawflies of the genera Diprion and Neodiprion, were proposed based on chemo-and stereoselective transformations of L-(-)-menthol derivatives. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 73–76, January–February, 2006.
Keywords:L-(-)-menthol  3R-dimethyloctan-6S-olide (mentholactone)  4R-menthenone  1-bromo-3S-methylundecane  2S-acetoxy-3S,7S-dimethylpentadecane [(S,S,S)-diprionylacetate]  synthon  pheromone  synthesis
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