79755-53-6Relevant academic research and scientific papers
Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid
Shi, Yiping,Kamer, Paul C. J.,Cole-Hamilton, David J.
supporting information, p. 1043 - 1053 (2019/03/12)
Cardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C-O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.
Synthesis of potential bisphenol A substitutes by isomerising metathesis of renewable raw materials
Trita,Over,Pollini,Baader,Riegsinger,Meier,Goo?en
supporting information, p. 3051 - 3060 (2017/07/15)
Isomerising metathesis is introduced as a sustainable method to produce dihydroxystilbene derivatives from eugenol, a clove oil ingredient, and cardanol from cashew nut shell liquid. Hydrogenation of the dihydroxystilbenes provided their di(hydroxyphenyl)ethane analogues. Initial studies to convert these monomers into polycarbonates and thiol-ene polymers support their potential to replace the petrol-derived bisphenol A (BPA). The estrogenic activity of the monomers derived from cardanol was found to be in the same range as that of BPA, a known endocrine disruptor. In contrast, eugenol-derived materials were found to be non-estrogenic, opening up new perspectives for bio-based food packaging materials.
Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis
Baader,Podsiadly,Cole-Hamilton,Goossen
supporting information, p. 4885 - 4890 (2015/01/08)
Starting from a purified cashew nut shell extract containing mostly anacardic acid derivatives, the tsetse fly attractants 3-ethyl- and 3-propylphenol were selectively synthesised. The mixture was first converted into 3-(non-8-enyl)phenol in 98% purity via ethenolysis and distillation with concomitant decarboxylation. The olefinic side chain was then shortened by isomerising cross-metathesis with short-chain olefins in the presence of a [Pd(μ-Br)(tBu3P)]2 isomerisation catalyst and a second-generation Hoveyda-Grubbs catalyst, and the synthesis was completed by a hydrogenation step.
Biosynthesis of Fungal Metabolites. Terrein, a Metabolite of Aspergillus terreus Thom
Hill, Robert A.,Carter, Rachel H.,Staunton, James
, p. 2570 - 2576 (2007/10/02)
Terrein, a metabolite of Aspergillus terreus Thom, is biosynthesised from 3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin by contraction of an aryl ring.The direction of the ring contraction has been investigated using acetate as precursor.
