- PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
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The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
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Paragraph 00348; 00364
(2021/12/08)
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- Synthesis of fluorine-containing prenylated benzophenones
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In this study, an effective route to synthesize fluorine-containing prenylated benzophenones was developed. Friedel–Crafts acylation and electrophilic aromatic substitution reactions were the key reactions of this synthesis to achieve these fluorinated prenylated benzophenones. The use of DBU in the prenylation step achieved only the C-prenylated benzophenones, whereas K2CO3 produced the C- and O-prenylated benzophenones.
- Mzozoyana, Vuyisa,van Heerden, Fanie R.
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p. 2226 - 2235
(2020/07/09)
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- gem-Diprenylation of Acylphloroglucinols by a Fungal Prenyltransferase of the Dimethylallyltryptophan Synthase Superfamily
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Aspergillus terreus aromatic prenyltransferase (AtaPT) catalyzes predominantly C-monoprenylation of acylphloroglucinols in the presence of different prenyl diphosphates. With dimethylallyl diphosphate (DMAPP) as prenyl donor, gem-diprenylated products 1D3, 2D3, and 3D3 were also detected. High conversion of 1D1 to 1D3, 2D1 to 2D3, and 3D1 to 3D3 was demonstrated by incubation with AtaPT and DMAPP. The first example of gem-diprenylation by a member of the dimethylallyltryptophan synthase superfamily is provided.
- Zhou, Kang,Wunsch, Carsten,Dai, Jungui,Li, Shu-Ming
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supporting information
p. 388 - 391
(2017/04/21)
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- Synthesis of 3-geranyl- and 3-prenyl-2,4,6-trihydroxybenzophenone
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Biologically active phenyl[3-(3,7-dimethyl-2,6-octadienyl)-2,4,6-trihydroxyphenyl]methanone (2) and phenyl[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]methanone (3) were synthesized by an efficient and convenient synthetic sequence. The reaction steps of this synthesis included methylation, Friedel-Crafts acylation, demethylation and geranylation steps.
- Mzozoyana, Vuyisa,van Heerden, Fanie R.
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supporting information
p. 599 - 603
(2017/03/15)
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- Friedel-Crafts Alkylation of Acylphloroglucinols Catalyzed by a Fungal Indole Prenyltransferase
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Naturally occurring prenylated acylphloroglucinol derivatives are plant metabolites with diverse biological and pharmacological activities. Prenylation of acylphloroglucinols plays an important role in the formation of these intriguing natural products and is catalyzed in plants by membrane-bound enzymes. In this study, we demonstrate the prenylation of such compounds by a soluble fungal prenyltransferase AnaPT involved in the biosynthesis of prenylated indole alkaloids. The observed activities of AnaPT toward these substrates are much higher than that of a microsomal fraction containing an overproduced prenyltransferase from the plant hop.
- Zhou, Kang,Ludwig, Lena,Li, Shu-Ming
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p. 929 - 933
(2015/05/05)
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- Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives
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In search for new methods aiming biomimetic synthesis of polyprenylated acylphloroglucinols (PPAPs), we now report the results of an evaluation of sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives, in neutral conditions. As a result, conditions were found for rather efficient C-prenylation of these compounds. The corresponding trimethyl ether gave the best results, but the reaction was accompanied by a deacylation process. Geranyl transfer was also observed, but in low yield, and, interestingly, an isolavandulyl group could be introduced with an appreciable yield.
- Brajeul, Solenn,Delpech, Bernard,Marazano, Christian
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p. 5597 - 5600
(2008/03/11)
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- The Synthesis of Some Novel Deoxyhumulone Analogues. Observations on the Air-oxidation of 2',4',6'-Trihydroxy-3'-isopentyl-5'-(3-methylbut-2-enyl)isovalerophenone and its corresponding Humulone Derivatives
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Two novel analogues of natural deoxyhumulone have been synthesised: (a) with the 3-methylbutanoyl side chain replaced by benzoyl, and (b) with the dimethylallyl substituents replaced by the cycloheptylidene analogues.Oxidation of these with air gave the c
- Cann, Martin R.,Davis, Anne-Marie,Shannon, Patrick V. R.
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p. 1413 - 1421
(2007/10/02)
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