Facile total synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide from carbohydrate, a mosquito oviposition attractant pheromone

Total synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide, a major component of mosquito oviposition attractant pheromones is reported. The key synthetic steps involve epoxide opening by lithiated salt of ethylpropionate and acid catalysed lactonization. The total synthesis was achieved in 11 linear steps staring from a readily available carbohydrate δ-gluconolactone in 18% overall yield making it simple, practical and elegant.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Total synthesis of (−)-(5R,6S)-6-acetoxy-5-hexadecanolide from carbohydrate, a mosquito oviposition attractant. ► Synthesis achieved in 11 reaction steps utilizing cheap and readily available δ-gluconolactone. ► Straight forward reaction conditions with overall yield of 18% makes the synthesis quite simple and convenient.