Stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadec-2-yl acetate and propionate, the sex pheromones of pine sawflies |
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| Authors: | Zikun Wang Weisheng Tian |
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| Institution: | a Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China
b Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, PR China |
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| Abstract: | The stereoselective synthesis of (2S,3S,7S)-3,7-dimethylpentadec-2-yl acetate (2) and propionate (3) was accomplished by utilizing the cheap and easily available chiron (R)-4-methyl-δ-valerolactone (4). The key steps were chelation-controlled addition of Gilmann reagent to chiral β-alkoxy aldehyde 12 and the Cu(I)-catalyzed coupling of Grignard reagent with bromoester 5 in the presence of NMP. |
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| Keywords: | Sex pheromones Pine sawflies Chiron Resource chemistry Chelation-controlled |
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