38228-28-3Relevant academic research and scientific papers
Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
supporting information, p. 18118 - 18127 (2020/11/26)
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
D3h-symmetrical hydrogen-bonding unit as a saccharide recognition and self-assembling module
Abe, Hajime,Horii, Asuka,Matsumoto, Shinya,Shiro, Motoo,Inouye, Masahiko
supporting information; experimental part, p. 2685 - 2688 (2009/05/26)
(Chemical Equation Presented) A D3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treate
The Diels-Alder approach towards cannabinoids
Lesch, Bernhard,Toraeng, Jakob,Nieger, Martin,Braese, Stefan
, p. 1888 - 1900 (2007/10/03)
Starting from the efficient synthesis of benzopyrans by base-catalyzed condensation reactions between substituted 2-hydroxybenzaldehydes and α,β-unsaturated aldehydes, thermal, Lewis acid catalyzed and enantioselective organo-promoted Diels-Alder reactions towards the tricyclic cannabinoid system are presented. The procedures are exemplified by the synthesis of a pentacycle and various tricycles respectively, in up to 95% enantiomeric excess and provide a versatile entry to this group of natural products with tetrahydrocannabinol (THC) being the most prominent one. Most published strategies are based on the formation of the tricyclic system by condensation between readily available phenols and monoterpenes, whereas we present a novel approach to cannabinoid derivatives based on a modular synthesis. Georg Thieme Verlag Stuttgart.
Synthesis of both enantiomers of hiburipyranone
Uchida, Kanako,Watanabe, Hidenori,Kitahara, Takeshi
, p. 8975 - 8984 (2007/10/03)
Both enentiomers of hiburipyranone, a cytotoxic metabolite of marine sponge, was synthesized employing Sharpless' asymmetric dihydroxylation as a key step and absolute configuration of the natural compound at C-3 position was determined to be R.
A simple synthesis of the natural 2,5-dialkylresorcinol free radical scavenger antioxidant: Resorstatin
Combes, Sebastien,Finet, Jean-Pierre
, p. 3769 - 3778 (2007/10/03)
3,5-Dimethoxybenzoic acid 3 has been transformed into olivetol dimethyl ether 6 in three steps in 79% yield. Directed ortho-metallation-alkylation of 6, followed by boron tribromide demethylation resulted in a simple and inexpensive synthesis of resorstatin, in 70% overall yield from 3.
5-Alkylresorcinols from Hakea trifurcata that cleave DNA
Lytollis, William,Scannell, Ralph T.,An, Haoyun,Murty,Reddy, K. Sambi,Barr, John R.,Hecht, Sidney M.
, p. 12683 - 12690 (2007/10/03)
A dichloromethane extract of Hakea trifurcata that mediated relaxation of ?X174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the acti
BIOLOGICALLY ACTIVE PHENOLIC METABOLITES OF A VERTICICLADIELLA SPECIES
Ayer, William A.,Browne, Lois M.,Lovell, Sarah H.
, p. 2267 - 2272 (2007/10/02)
The metabolites produced when a Verticicladiella species (Canadian Forestry Service strain C728), the causative agent of the black stain root disease of many conifers, is grown in liquid culture have been investigated.Orcinol, orcinol monomethyl ether, 1,3,6,8-tetrahydroxyanthraquinone, and the α-L-rhamnopyranosides of orcinol and orcinol methyl ether have been isolated and indentified.Orcinol methyl ether and its rhamnoside both show antibacterial activity and orcinol methyl ether also inhibits the growth of pine germlings.The general antibacterial activity of 5-alkylresorcinols and their monomethyl ethers is reported.-Key Word Index-Verticicladiella sp.; Deuteromycontina; blue-stain fungus; phytotoxin; phenols; methylorcinol rhamnoside; phenol monomethyl ethers; antiseptics.
Long Chain Phenols. Part 17. The Synthesis of 5-resorcinol, 'Cardol monoene,' and of 5-resorcinol Dimethyl Ether, 'Cardol diene' Dimethyl Ether
Baylis, Christopher J.,Odle, Stanley W.,Tyman, John H. P.
, p. 132 - 141 (2007/10/02)
Two unsaturated compounds in the 'cardol' series, an important component phenol from Anacardium Occidentale, have been synthesised. 3,5-Dimethoxybenzaldehyde interacted with OH-protected 6-chlorohexan-1-ol in the presence of lithium to give, after acidic treatment, 1-(3,5-dimethoxyphenyl)heptane-1,7-diol which was hydrogenolysed selectively to 7-(3,5-dimethoxyphenyl)heptan-1-ol.Conversion into the bromide and alkylation of lithio-oct-1-yne gave 5-(pentadec-8-ynyl)resorcinol dimethyl ether which was selectively converted into the 8-(Z)-alkene.Dmethylation with lithium iodide gave 5-resorcinol which was identical to 'cardol monoene'.Reaction of 7-(3,5-dimethoxyphenyl)heptyl bromide with lithium derivative of OH-protected propargyl alcohol, gave after acidic treatment 10-(3,5-dimethoxyphenyl)dec-2-yn-1-ol, the bromide of which with pent-1-ynylmagnesium bromide afforded 5-pentadec-8,11-diynylresorcinol dimethyl ether.Selective hydrogenation yielded 5-resorcinol dimethyl ether identical with the dimethyl ether of 'cardol diene.'
