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Synlett 1996; 1996(6): 511-512
DOI: 10.1055/s-1996-5478
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Enantioselective Synthesis of (3S,4S)-4-Methyl-3-heptanol, a Beetle Pheromone, via the Regioselective Cleavage of an α-Epoxy Oxazolidine

C. Agami, F. Couty* , O. Venier
  • *Laboratoire de Synthèse Asymétrique, Université P. et M. Curie, Case 47, 4 place Jussieu, 75005 Paris, France
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Publication Date:
31 December 2000 (online)

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Chiral α-epoxy oxazolidines derived from (R)-phenyl glycinol were reacted with organo cuprates in a totally regio and stereoselective way. This key-step sustained the synthesis of enantiopure (3S,4S)-4-methyl-3-heptanol, a beetle aggregation pheromone, and of its (3S,4R) anti stereisomer, the enantiomer of an ant trail pheromone.

oxazolidine - organo cuprates - pheromones - torsional strain - dipolar repulsion

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