25974-58-7Relevant academic research and scientific papers
Total synthesis of the novel antifungal agent (±)-jesterone
Mehta, Goverdhan,Pan, Subhas Chandra
, p. 811 - 813 (2004)
A total synthesis of the novel, biologically active epoxyquinone natural product (±)-jesterone has been accomplished from the readily accessible Diels-Alder adduct of cyclopentadiene and prenylated-p-benzoquinone. The approach delineated here is notable f
Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids
Lu, Yanhui,Nakatsuji, Hidefumi,Okumura, Yukimasa,Yao, Lu,Ishihara, Kazuaki
supporting information, p. 6039 - 6043 (2018/05/14)
Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.
Highly Selective Synthesis of Ortho-Prenylated Phenols and Chromans by using a New Bimetallic CuAl-KIT-5 with a 3D-Cage-type Mesoporous Structure
Varghese, Shaji,Anand, Chokkalingam,Dhawale, Dattatray,Mane, Gurudas P.,Wahab, Mohammad A.,Mano, Ajayan,Raj, George Allen Gnana,Nagarajan, Samuthira,Vinu, Ajayan
, p. 899 - 902 (2013/05/08)
A nice piece of KIT: The first synthesis of a new bimetallic 3D-cage-type mesoporous catalyst CuAl-KIT-5 and its remarkable performance for the highly selective synthesis of ortho-prenylated phenols and chromans is reported.
Gold-catalyzed intramolecular hydroarylation of olefins. Scope evaluation and preliminary mechanistic studies
Jean, Mickael,Van De Weghe, Pierre
, p. 3509 - 3513 (2011/07/09)
We report a gold-catalyzed intramolecular hydroarylation of unactivated olefins using a combination of AuCl3/AgOTf as the catalytic system affording dihydrobenzopyrans, tetralins and tetrahydroquinolines in good yields. For our preliminary mechanistic studies, we have investigated the kinetic isotope effects with deuterated arene compounds and found that this catalytic hydroarylation is consistent with an electrophilic aromatic substitution process.
Regioselective iron-catalyzed decarboxylative allylic etherification
Trivedi, Rushi,Tunge, Jon A.
scheme or table, p. 5650 - 5652 (2010/02/28)
[Chemical Equation Presented] An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via π-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.
Alternative Lewis acids to effect Claisen rearrangement
Sharma,Ilangovan,Sreenivas, Punna,Mahalingam
, p. 615 - 618 (2007/10/03)
Yb(OTf)3 and DIBAL-H are developed as alternative Lewis acids for effecting Claisen rearrangement of allyl, crotyl and prenyl aryl ethers.
Reaction between phenols and isoprene under zeolite catalysis. Highly selective synthesis of chromans and o-isopentenylphenols
Bigi, Franca,Carloni, Silvia,Maggi, Raimondo,Muchetti, Chiara,Rastelli, Massimo,Sartori, Giovanni
, p. 301 - 304 (2007/10/03)
Chromans 3 and o-isopentenylphenols 4 are synthesized in satisfactory to good yields and selectivities by the reaction of phenols and isoprene in the presence of the commercially available acid faujasite zeolite HSZ-360.
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
CHROMENES AND CHROMANONES. PART II. THE BIRCH REDUCTION OF PRECOCENE I AND PRECOCENE II
Aniol, Miroslaw,Wawrzenczyk, Czeslaw
, p. 2655 - 2662 (2007/10/02)
The reduction of precocene I (1a), precocene II (1c) and 6-methoxy-2,2-dimethyl-2H-chromene (1b) with sodium or lithium in liquid ammonia was examined.The phenolic compounds and the bicyclic one with partialy reduced benzene ring were obtained as the majo
Total synthesis of 2-tetraprenylbenzoquinol and -benzoquinone
Bouzbouz,Kirschleger
, p. 714 - 718 (2007/10/02)
The total synthesis of 2-tetraprenylbenzoquinol and -benzoquinone is described. A key step in this synthesis is the highly regio- and stereoselective coupling between an appropriate aromatic allylcarbonate and an activated bifunctional farnesyl derivative
