612-17-9Relevant articles and documents
Rabideau,Burkholder
, p. 4283,4286 (1978)
A Simple Preparation of Benzo-Fused Bicycloalkadienes from 1,3-Diene-Benzoquinone Cycloadducts
Schmid, George H.,Rabai, Jozsef
, p. 332 - 333 (1988)
Synthetic procedures are reported for the conversion of the Diels-Alder adduct of benzoquinone and both 1,3-cyclohexadiene and 1,3-cycloheptadiene to the parent hydrocarbons, 1,4-dihydro-1,4-ethanonaphthalene (benzobicyclooctadiene) and 6,7,8,9-tetrahydro-5H-5,9-ethenobenzocycloheptene (benzobicyclononadiene), respectively.The Diels-Alder adducts can be conveniently converted into the 5,8- and 1,4-dimethoxy as well as 5,8- and 1,4-diacetoxy derivatives, respectively, of these tricyclic compounds.
Wideman,L.G.
, p. 1698 - 1699 (1970)
Garst,Pacifici
, p. 1802 (1975)
Dearomatization of naphthalene: Stereoselective cis-1,4 tandem additions promoted by osmium(II)
Winemiller, Mark D.,Harman, W. Dean
, p. 7835 - 7840 (1998)
The naphthalene complex of pentaammineosmium(II) (1) reacts with four different classes of electrophiles to form 1-naphthalenium species 2-5. These η3-allyl complexes react stereospecifically with a variety of nucleophiles to form cis-1,4-dihydronaphthalene complexes. The entire reaction sequence may be performed outside a glovebox in two steps using conventional techniques.
Stereoconvergent generation of a contrasteric syn-bicyclopropylidene (=syn-Cyclopropylidenecyclopropane) by stille-like coupling
Gueney, Murat,Essiz, Selcuk,Dastan, Arif,Balci, Metin,De Lucchi, Ottorino,Sahin, Ertan,Fabris, Fabrizio
, p. 941 - 950 (2013)
Stereoisomerically pure endo- and exo-7-halo-7-(trimethylstannyl) benzonorcar-3-enes (=endo- and exo-(1-halo-1a,2,7,7a-tetrahydro-1H-cyclopropa[b] naphthalen-1-yl)trimethylstannane) 4 and 6 were selectively obtained by lithium-tin or magnesium-tin transmetalation in good yields (Scheme 2 and 3). The reaction of these compounds with copper(I) thiophene-2-carboxylate (CuTC) produced in both cases the corresponding CS-symmetric bicyclopropylidene (=cyclopropylidenecyclopropane) syn-1, a single diastereoisomer (Schemes 5 and 6). The structure of syn-1 was undoubtedly elucidated by X-ray single crystal diffraction. The coupling mechanism of the carbenoid cyclopropane is discussed (Scheme 7). Copyright
Dibenzoate esters of cis-tetralin-2,3-diol as analogs of (-)-epigallocatechin gallate: Synthesis and crystal structure of anticancer drug candidates
Chan, Tak-Hang,Fukumoto, Kozo,Nishioka, Takanori,Renzetti, Andrea,Rutherford, Ryan Noboru,Ura, Shinji
, p. 1085 - 1095 (2020/12/15)
(-)-Epigallocatechin gallate (EGCG), the main component of green tea extract, displays multiple biological activities. However, it cannot be used as a drug due to its low cellular absorption, instability and metabolic degradation. Therefore, there is a need to provide analogs that can overcome the limitations of EGCG. In this work, six synthetic analogs of EGCG sharing a common tetralindiol dibenzoate core were synthesized and fully characterized by 1H NMR, 13C NMR, HRMS and IR spectroscopies, and X-ray crystallography. These are (2R,3S)-1,2,3,4-tetrahydronaphthalene-2,3-diyl bis[3,4,5-tris(benzyloxy)benzoate], C66H56O10, and the analogous esters bis(3,4,5-trimethoxybenzoate), C30H32O10, bis(3,4,5-trifluorobenzoate), C24H14F6O4, bis[4-(benzyloxy)benzoate], C38H32O6, bis(4-methoxybenzoate), C26H24O6, and bis(2,4,6-trifluorobenzoate), C24H14F6O4. Structural analysis revealed that the molecular shapes of these dibenzoate esters of tetralindiol are significantly different from that of previously reported dimandelate esters or monobenzoate esters, as the acid moieties extend far from the bicyclic system without folding back over the tetralin fragment. Compounds with small fluorine substituents take a V-shape, whereas larger methoxy and benzyloxy groups determine the formation of an L-shape or a cavity. Intermolecular interactions are dominated by π-π stacking and C-H..π interactions involving the arene rings in the benzoate fragment and the arene ring in the tetrahydronaphthalene moiety. All six crystal structures are determined in centrosymmetric space groups (either P, P21/n, C2/c or I2/a).
Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock
Uthoff, Florian,L?we, Jana,Harms, Christina,Donsbach, Kai,Gr?ger, Harald
, p. 4856 - 4866 (2019/05/02)
Ozanimod represents a recently developed, promising active pharmaceutical ingredient (API) molecule in combating multiple sclerosis. Addressing the goal of a scalable, economically attractive, and technically feasible process for the manufacture of this drug, a novel alternative synthetic approach toward (S)-4-cyano-1-aminoindane as a chiral key intermediate for ozanimod has been developed. The total synthesis of this intermediate is based on the utilization of naphthalene as a readily accessible, economically attractive, and thus favorable petrochemical starting material. At first, naphthalene is transformed into 4-carboxy-indanone within a four-step process by means of an initial Birch reduction, followed by an isomerization of the C=C double bond, oxidative C=C cleavage, and intramolecular Friedel-Crafts acylation. The transformation of the 4-carboxy-indanone into (S)-4-cyano-1-aminoindane then represents the key step for introducing the chirality and the desired absolute S configuration. When evaluating complementary biocatalytic approaches based on the use of a lipase and transaminase, respectively, the combination of a chemical reductive amination of the 4-carboxyindanone followed by a subsequent lipase-catalyzed resolution turned out to be the most efficient route, leading to the desired key intermediate (S)-4-cyano-1-aminoindane in satisfactory yield and with excellent enantiomeric excess of 99%.
