- SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
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In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
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- Syntheses of the sex pheromone of the codling moth
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Grignard coupling between appropriated synthons afforded (E, E)-8, 10-dodecadien-1-ol (1) the sex attractant pheromone of the Codling moth (Laspeyresia pomonella) a notorious pest of the apple orchards. The synthons used in this paper were (E,E)-2,4-hexadien-1-yl bromide (4, sorbyl bromide), (E,E)-2,4-hexadien-1-yl acetate (5, sorbyl acetate) and 6-bromohexan-1-ol protected as tetrahydropyranyl ether (8) or trimethylsilyl ether (9). The product 1 and the intermediate synthons were characterised by their IR, 1H and 13C-NMR and MS spectra.
- Popovici, Nicolae
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p. 221 - 224
(2007/10/03)
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- Synthesis of dodeca-8E,10E-dien-1-ol - The sex pheromone of Laspeyresia pomonella via the acetolysis of 4-propenyl-1,3-dioxane
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A new scheme has been developed for the synthesis of dodeca-8E,10E-dien-1-ol (the sex pheromone of the codling moth) from sorbyl acetate, available from 4-propenyl-1,3-dioxane through the intermediate diacetate of 3-propenyl-2-oxapentane-1,5-diol.
- Shakova,Zorin,Musavirov,Safarov,Muslukhov,Kharisov,Ishmuratov,Rakhmankulov
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p. 582 - 584
(2007/10/03)
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- A NEW SYNTHESIS OF THE PHEROMONE OF THE CODLING MOTH - DODECA-8E,10E-DIEN-1-OL - VIA AN ENYNIC INTERMEDIATE
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A new method has been developed for the synthesis of the main component of the pheromone of the codling moth - dodeca-8E,10E-dien-1-ol - using in the key stages Wittig reactions and the trans-hydride reduction of the triple bond of an intermediate enynol.
- Khrimyan, A. P.,Makaryan, G. M.,Ovanisyan, A. L.,Wimmer, Z.,Romanyuk, M.,et al.
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p. 103 - 108
(2007/10/02)
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