70219-84-0Relevant academic research and scientific papers
PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
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Paragraph 00348; 00368, (2021/12/08)
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).
Synthesis of fluorine-containing prenylated benzophenones
Mzozoyana, Vuyisa,van Heerden, Fanie R.
, p. 2226 - 2235 (2020/07/09)
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.
Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone
Pepper, Henry P.,Tulip, Stephen J.,Nakano, Yuji,George, Jonathan H.
, p. 2564 - 2573 (2014/04/17)
A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.
Biomimetic total synthesis of (±)-garcibracteatone
Pepper, Henry P.,Lam, Hiu C.,Bloch, Witold M.,George, Jonathan H.
, p. 5162 - 5164,3 (2012/12/12)
The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.
Biomimetic total synthesis of (±)-garcibracteatone
Pepper, Henry P.,Lam, Hiu C.,Bloch, Witold M.,George, Jonathan H.
, p. 5162 - 5164 (2013/01/15)
The polycyclic polyprenylated acylphloroglucinol natural product garcibracteatone has been synthesized in four steps from phloroglucinol, using a strategy based on biosynthetic speculation. The key biomimetic transformation is a cascade of 7-endo-trig and 5-exo-trig radical cyclizations followed by a terminating aromatic substitution reaction.
Rapid access to polyprenylated phloroglucinols via alkylative dearomatization-annulation: Total synthesis of (±)-clusianone
Qi, Ji,Porco Jr., John A.
, p. 12682 - 12683 (2008/03/14)
A concise approach to the bicyclo[3.3.1]nonane framework of the polyprenylated phloroglucinol natural products utilizing a tandem alkylative dearomatization-annulation sequence is described. Syntheses of (±)-clusianone and a complex adamantane framework h
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
Cann, Martin R.,Davis, Anne-Marie,Shannon, Patrick V. R.
, p. 1413 - 1421 (2007/10/02)
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
Synthesis of Vismiaphenone-B: A Naturally Occurring Prenylated Benzophenone
Pathak, V. P.,Khanna, R. N.
, p. 253 - 254 (2007/10/02)
Vismiaphenone-B, 5-C-prenyl-2,6-dihydroxy-6'',6''-dimethylchromenobenzophenone (II), has been synthesised starting from 2,4,6-trihydroxybenzophenone (V).V on prenylation with prenyl bromide in the presence of methanolic sodium methoxide yields three products, viz. 3,5-di-C-prenyl-2,4,6-trihydroxybenzophenone (VI), 2,6-dihydroxy-4-O-prenylbenzophenone (VII) and a brown oil, which could not be characterised.VI on cyclodehydrogenation with DDQ affords II, identical in all respects (UV, IR and PMR) with a natural sample.
Synthesis of Naturally Occurring Prenylated Benzophenones. Vismiaphenone A, Vismiaphenone B, and Isovismiaphenone B
Pathak, Ved Prakash,Khanna, Rajinder Nath
, p. 2264 - 2266 (2007/10/02)
2,4,6-Trihydroxybenzophenone on prenylation with 2-methyl-3-buten-2-ol in the presence of (C2H5)2O*BF3 yielded 2,4,6-trihydroxy-3,5-diprenylbenzophenone (3), 2,6-dihydroxy-4-prenyloxybenzophenone, 2,6-dihydroxy-3-prenyl-4-prenyloxybenzophenone, a benzodip
