79233-10-6Relevant articles and documents
Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
Bering, Luis,Jeyakumar, Kirujan,Antonchick, Andrey P.
, p. 3911 - 3914 (2018/07/22)
A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.
Catalytic asymmetric bromocyclization of polyenes
Samanta, Ramesh C.,Yamamoto, Hisashi
supporting information, p. 1460 - 1463 (2017/02/10)
The first catalytic asymmetric bromonium ion-induced polyene cyclization has been achieved by using a chiral BINOL-derived thiophosphoramide catalyst and 1,3-dibromo-5,5-dimethylhydantoin as an electrophilic bromine source. Bromocyclization products are o
Organic Photocatalytic Cyclization of Polyenes: A Visible-Light-Mediated Radical Cascade Approach
Yang, Zhongbo,Li, Han,Zhang, Long,Zhang, Ming-Tian,Cheng, Jin-Pei,Luo, Sanzhong
, p. 14723 - 14727 (2015/10/19)
A visible-light-mediated, organic photocatalytic stereoselective radical cascade cyclization of polyprenoids is described. The desired cascade cyclization products are achieved in good yields and high stereoselectivities with eosinY as photocatalyst in hexafluoro-2-propanol. The catalyst system is also suitable for 1,3-dicarbonyl compounds, which require only catalytic amounts of LiBr to promote the formation of the corresponding enols.
Biomimetic synthesis of thiaplidiaquinones A and B
Khalil, Iman M.,Barker, David,Copp, Brent R.
, p. 2256 - 2260 (2013/02/25)
A biomimetic synthesis of the biologically active ascidian metabolites thiaplidiaquinones A and B is described. Reaction of geranylbenzoquinone with Et3N in CH2Cl2 yielded two isomeric quinones, comprising the benzo[c]chro
Chiral Lewis base-assisted Bronsted acid (LBBA)-catalyzed enantioselective cyclization of 2-geranylphenols
Sakakura, Akira,Sakuma, Masayuki,Ishihara, Kazuaki
supporting information; experimental part, p. 3130 - 3133 (2011/07/31)
Chiral Lewis base-assisted Bronsted acids (Chiral LBBAs) have been designed as new organocatalysts for biomimetic enantioselective cyclization. A salt of a chiral phosphonous acid diester with FSO3H catalyzes the enantioselective cyclization of
Total synthesis of polyprenylhydroquinols and benzoquinones
Bouzbouz, Samir,Kirschleger, Bernard,Villieras, Jean
, p. 67 - 84 (2007/10/03)
The total synthesis of polyprenylhydroquinols and benzoquinones is described.First, two appropriate aromatic allyl carbonates (moieties with one and two prenyls) and two activated bifunctional terpenyl derivatives (moieties with two and three prenyls) were synthesized.These molecules were then reacted together using a highly regio- and stereoselective coupling with Pd(PPh3)4 as a catalyst.The synthesis was achieved by functional group elimination and formation of quinonic and hydroquinonic moieties. - Keywords: polyprenylbenzoquinol; polyprenylhydroquinone; allylcarbonate; ?-allyl palladium complex
Acid-catalysed Intramolecular Cyclization of Geranyl Hydroquinone Derivatives from Cordia alliodora. X-Ray Crystal and Molecular Structure of 1,2,3,3a,4,9,10,10a-Octahydro-5,8-dimethoxy-3,10-dimethyl-3a,9-epoxybenzazulene
Manners, Gary D.,Wong, Rosalind Y.
, p. 1849 - 1854 (2007/10/02)
The aqueous acid-catalysed intramolecular cyclization of dimethylated alliodorin (2) obtained from the heartwood of Cordia alliodora has been characterized by X-ray analysis as the unusual tetracyclic di-O-methyl hydroquinone title compound (8).A new synthesis of di-O-methylalliodorin (2) from a terminal methylallylic sulphide derivative of 2-geranil-1,4-dimethoxybenzene is described. Crystals of the title compound (8) are monoclinic, space group P21/c, unit cell dimensions a = 14.984(7), b = 5.206(4), c = 20.131(9) Angstroem, β = 99.77(1) deg, Z = 4.The structure was solved by direct methods and refined by least-squares calculations to an R value of 0.078 for 1 832 independent reflections measured on a diffractometer using Cu-Kα radiation.
