Stereoselective synthesis of (−)-6-acetoxyhexadecanolide: a mosquito oviposition attractant pheromone

The stereoselective synthesis of (−)-6-acetoxyhexadecanolide was achieved from the readily available chiral pool compound, l-(+)-tartaric acid. The synthetic sequence includes the elaboration of an α-benzyloxy aldehyde derived from tartaric acid with ring closing metathesis as the key step.

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(4R,5R)-4-Acryloxy-5-benzyloxypentadec-1-eneC25H38O3[α]D = +13.0 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (4R,5R)

(R)-6-((R)-1-(Benzyloxy)undecyl)-5,6-dihydropyran-2-oneC23H34O3[α]D = +61.9 (c 2.1, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5R,6R)

(−)-(5R,6S)-6-Acetoxy-5-hexadecanolideC18H32O4[α]D = −37.5 (c 0.4, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5R,6S)