A new synthetic route for the preparation of the insecticidal compound 2-hexadecylfuran is described in this study. The procedure starts from readily available furfuraldehyde and palmitic anhydride via two steps employing the Perkin reaction and resulting in a 25% overall yield. The method can be deemed as a practical and environmentally friendly route to prepare a potentially important class of insecticide.
A practical and environmentally friendly route to prepare a potentially important class of insecticide.
A two-step synthesis of the insect anti-feedant 2-hexadecylfuran (1) was accomplished starting from inexpensive furfuraldehyde (2)19–21 in 25% overall yield. Although the yield is low, the starting materials are inexpensive and are obtained from domestic agricultural sources.
This is how I prefer my avocados!
- Avocado is Incredibly Nutritious. …
- They Contain More Potassium Than Bananas. …
- Avocado is Loaded With Heart-Healthy Monounsaturated Fatty Acids. …
- Avocados Are Loaded With Fiber. …
- Eating Avocados Can Lower Cholesterol and Triglyceride Levels.
Fortunately, avocadofuran is synthesised from FURFURAL and so we can continue to enjoy the culinary benefits of avocados.
The avocadofurans are a family of natural products isolated from avocado (Persia) which consist of 2-alkylfurans with varying degrees and sites of unsaturation (double and triple bonds) in the alkyl chain.1–3 Rodriguez-Soana and co-workers demonstrated that compounds structurally related to avocadofurans, saturated 2-alkylfurans with chain length of 14–18 carbon atoms, have inhibitory activity against larval growth of the agricultural insect beet army worm (Spodoptera exigua) and, therefore, such compounds could be useful insecticides in crop protection.4,5 The synthetic route employed by Rodriguez-Soana et al. to prepare 2-hexadecylfuran (1) is shown in Scheme 1. Furan is deprotonated at the alpha-position by reaction with butyllithium at cryogenic temperature, afterwards 1-bromohexadecane was added for a nucleophilic substitution reaction.
- A new synthesis route for the preparation of the avocadofuran, 25.09.2016