- A Short and Efficient Synthesis of Crocetin-dimethylester and Crocetindial
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In this paper we describe an efficient six-step synthesis of crocetin-dimethylester that could be further reduced to a "four-step" synthesis through the use of in situ procedures. The simplicity of the whole process, the ready availability of starting materials, and the high overall yield render this strategy a very attractive synthesis of this very important compound, which is the key intermediate for the synthesis of several carotenoids and other polyene natural products.
- Frederico, Daniel,Marcos Donate, Paulo,Gomes Constantino, Mauricio,Soares Bronze, Erika,Sairre, Mirela I.
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- C5 BENZOTHIAZOLYL SULFONE COMPOUND, METHOD OF PREPARING THE SAME, METHOD OF PREPARING POLYENE DIALDEHYDE COMPOUND USING THE SAME, AND METHOD OF SYNTHESIZING LYCOPENE USING THE SAME
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Disclosed are a novel C5 benzothiazolyl sulfone compound having an acetal protecting group, a method of preparing the same, and a method of efficiently preparing an apo-carotene dialdehyde compound having a polyene dialdehyde structure using the same. Also, a method of efficiently preparing lycopene by olefination (Julia-Kocienski) between the apo-carotene dialdehyde compound (C20 crocetin dialdehyde) and C10 benzothiazolyl geranyl sulfone is provided.
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- Sulfone-mediated syntheses of crocetin derivatives: Regioselectivity of highly functionalized building blocks
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New C5 sulfone building blocks containing a masked polar end group have been devised for the efficient synthesis of carotenoids with polar termini. Chemoselectivity or the regiochemical issue of the highly functionalized units has been carefully addressed depending on the soft or hard nature of electrophiles. These building blocks have been successfully applied to the syntheses of crocetin derivatives, crocetin dial and the novel crocetin dinitrile.
- Oh, Eun-Taek,Kim, Young-Hun,Jin, Jingquan,Su, Liang,Seo, Jung-Ah,Koo, Sangho
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p. 4712 - 4717
(2014/06/09)
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- Methods for synthesis of carotenoids, including analogs, derivatives, and synthetic and biological intermediates
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A method for synthesizing intermediates for use in the synthesis of carotenoid synthetic intermediates, carotenoid analogs, and/or carotenoid derivatives. The carotenoid analog, derivative, or intermediate may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include methods for synthesizing chemical compounds including an analog or derivative of a carotenoid. Carotenoid analogs or derivatives may include acyclic end groups. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.
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Page/Page column 38-39; 14-15
(2008/12/08)
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- METHODS FOR SYNTHESIS OF CHIRAL INTERMEDIATES OF CAROTENOIDS, CAROTENOID ANALOGS, AND CAROTENOID DERIVATIVES
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A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids.
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Page/Page column 47
(2010/10/20)
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- Trans carotenoids, their synthesis, formulation and uses
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The invention relates to trans carotenoid compounds and salts thereof as well as compositions thereof, methods for making them, and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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Page/Page column 31
(2008/06/13)
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- Synthesis of aryl-terminated polyenaldehydes and polyenetriethoxysilanes for preparation of self-assembled monolayers on silicon surfaces
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The synthesis of αω-terminally functionalized polyenes with arenes or hetarenes at one end and either an aldehyde or a triethoxysilyl function at the other end, capable of reacting with H-terminated or oxidized silicon surfaces, is described. Analogous to known Wittig reactions, polyenedialdehydes 1 and 3, the latter derived from 1 and phosphonium chloride 2 in a twofold Wittig olefination, were converted with phosphonium bromides 4 to give the (all-E)-arylpolyenaldehydes 5 and 6. A terminal alkyl chain was introduced in dialdehydes 1a and 3a by reaction with P,P-didecyldibenzophospholium bromide 8, resulting in polyenals 9. Wittig olefination of 5c and 9a with phosphonium chloride 2 afforded the (2-thienyl)tridecahexaenal 7 and the docosahexaenal 10. With respect to monolayer formation on oxidized Si(100) surfaces, (9-anthryl)- and (2-thienyl)-ω-functionalized polyenetriethoxysilanes 16 and 17 were prepared in a reaction sequence involving the introduction of a terminal triple bond with [3-(trimethylsilyl)prop-2-ynyl]triphenylphosphonium bromide (11), desilylation of the resulting arylpolyeninetrimethylsilanes 12, 13 with Bu4NF·3H2O, and subsequent hydrosilylation of the arylpolyenines 14, 15 using triethoxysilane under dichlorocyclooctadienylplatinum(II) catalysis.
- Effenberger,Wezstein
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p. 1368 - 1376
(2007/10/03)
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