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.
Division of Natural Product Chemistry, Indian Institute of Chemical Technology (CSIR), Hyderabad, AP, India.
Saibal
S
Das
Anand Kumar
AK
Mishra
Ashish
A
Kumar
Ahamad Al Khazim
AA
Al Ghamdi
Jhillu Singh
JS
Yadav
D000818:Animals; D009033:Culicidae; D005260:Female; D015394:Molecular Structure; D010058:Oviposition; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry*
D010675:Pheromones; D011753:Pyrones; C091336:6-acetoxy-5-hexadecanolide