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Synthesis 1997; 1997(5): 509-511
DOI: 10.1055/s-1997-1228
short paper
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An Enantiocontrolled Synthesis of Both Enantiomers of Frontalin

Takahiko Taniguchi, Keiichi Nakamura, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81(22)2176845; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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Both (+)- and (-)-enantiomers of frontalin, the aggregation pheromone of the Dendroctonus pine beetles, have been synthesized in an enantiocontrolled way from 2-acetyl-5-methylfuran by use of the Sharpless asymmetric dihydroxylation and the oxidative ring-expansion reactions as key steps.

frontalin - insect pheromone - asymmetric dihydroxylation - oxidative furan-ring expansion - chiral 6,8-dioxabicyclo[3.2.1]octance ring system