Asymmetric synthesis of (2R)- and (2S)-2-iodohexadecanal, natural inhibitors of the thyroid gland metabolism

Jacoby, C.; Braekman, Jean Claude; Daloze, Désiré

doi:10.1016/0040-4020(96)00582-0

Cited by 9 publications

(6 citation statements)

References 34 publications

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“…Colorless oil, 195 mg, yield 81%; R f value: (pet. ether:diethyl ether = 9:1) 0.41; 1 H-NMR (CDCl 3 ) δ 2.87–2.79 (m, 1H, OCH), 2.66 (dd, J = 5.1, 4.0 Hz, 1H, OC H H), 2.38 (dd, J = 6.0, 2.0 Hz, 1H, OC H H), 1.58–0.98 (m, 26H, 13 × CH 2 ), 0.83 (t, J = 6.4 Hz, 3H, CH 3 ); 13 C-NMR (CDCl 3 ) δ 52.1, 46.8, 32.4, 31.8, 29.6, 29.5, 29.4, 29.3, 25.9, 22.6, 13.9 [38].…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Organocatalysis-Based Synthesis of 3-Hydroxy Fatty Acids and Fatty γ-Lactones

et al. 2019

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3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

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Section: Methodsmentioning

confidence: 99%

Enantioselective Organocatalysis-Based Synthesis of 3-Hydroxy Fatty Acids and Fatty γ-Lactones

et al. 2019

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“…Coumpound 2 resulted from O-alkylation of the 7-hydroxy group of compound 6 with bromoacetaldehyde dimethyl acetal using sodium hydride as a base 10 followed by hydrolysis of the acetal functionality of 9 to the corresponding aldehyde with trifluoroacetic acid in a biphasic system. 11 Finally, 5-MOP (1) was obtained by the cyclization of the aldehydic compound 2 to form the furan ring according to the procedure described by Chimichi. 8 Repeated modifications of this general procedure for synthesis of the psoralens did not allow us to obtain a yield better than 40% of the linear furocoumarin 1 due to the increase in angular furocoumarin's proportion which was a result of a thermodynamically controlled process faced with the 5methoxy group.…”

Section: Methodsmentioning

confidence: 99%

Efficient Total Synthesis of 5-Methoxypsoralen

Roux¹,

Makki²,

Bévalot³

et al. 2007

Synlett

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“…Moreover, the biosynthesis and inhibitory activity have been shown to be unstereoselective. 191 Another a-iodoaldehyde, 2-iodooctadecanal (174), was also detected in rat and dog thyroids, where it was even more abundant than 2-IHDA (172). 186 6-Iodo-5-hydroxy-eicosatrienoic acid, d-lactone (175) and 5-iodo-4-hydroxydocosapentaenoic acid, g-lactone (176) have been identied in the thyroid gland of dogs.…”

Section: Mangaladossmentioning

confidence: 99%