Cyclotrimerization of 'Oxabenzonorbornadiene': Synthesis of syn- and anti-5,6,11,12,17,18-hexahydro-5,18:6,11 : 12,17-triepoxytrinaphthylene

De Lucchi, O
Dastan, A
Altundas, A
Fabris, F
Balcı, Metin
An efficient synthetic route to the concave-shaped, potentially ionophoric syn- and anti-isomers of 5,6,11,12,17,18-hexahydro-5,18:6,11:12,17-triepoxytrinaphthylene (4) was elaborated. Starting from 'oxabenzonorbornadiene' (5), the stannylated precursor 9 was prepared in three steps, followed by cyclotrimerization ;catalyzed by copper(I) thiophene-2-carboxylate (CuTC), which afforded 4 in a synlanti ratio of 5:4.


Synthesis, characterization, crystal and molecular structure of 1,5-Dihydro-2H-cyclopenta[1,2-b : 5,4-b ']dipyridin-2-imine
Baysal, Akin; Durap, Feyyaz; Gumgum, Bahattin; Yildirim, Leyla T.; Ulku, Dincer; Boga, Ayse Dilek; Özkar, Saim (Wiley, 2007-01-01)
The reaction of 1,5-diliydro-2H-cyclopenta[1,2-b:5,4-b'ldipyridin-2-one (3) with an alkylamine (butvlamine, hexylamine or ethylenediamine) yields, quite unexpectedly and in the absence of catalyst, the novel compound 1,5-dihydro-2H-cyclopentafl,2-b:5.4-b']dipyridin-2-imine (4) as the sole, analytically pure, solid product, which was fully characterized. The structure of 4 was unequivocally solved by single-crystal X-ray-diffraction analysis. The compound crystallizes in a monoclinic cell (space group P 2(1/...
Enantioselective synthesis of 2-(2-arylcyclopropyl)glycines: Conformationally restricted homophenylalanine analogs
Demir, Ayhan Sıtkı; Sesenoglu, O; Ulku, D; Arici, C (Wiley, 2004-01-01)
Starting from simple aromatic aldehydes and acetylfuran, (E)-1-(furan-2-yl)-3-arylprop-2-en-1-ones (2) were synthesized in high yields. Cyclopropanation of the C=C bond with trimethylsulfoxonium iodide (Me3SO+I-) furnished (furan-2-yl)(2-arylcyclopropyl)methanones 3 in 90-97% yields. Selective conversion of cyclopropyl ketones to their (E)- and (Z)-oxime ethers 5 and oxazaborolidine-catalyzed stercoselective reduction of the C-N bond followed by separation of the formed diastereoisomers, furnished (2-arylcy...
Chemistry of the benzotropone endoperoxides and their conversion into tropolone derivatives: Unusual endoperoxide rearrangements
Guney, M; Dastan, A; Balcı, Metin (Wiley, 2005-01-01)
The chemistry of two bicyclic endoperoxides, obtained by photooxygenation of 2,3-benzotropone (= 5H-benzocyclohepten-5-one 5) and of its ethyl carboxylate derivative 15, was investigated with the aim of synthesizing the respective benzotropolone derivatives. The reaction of the endoperoxide 10 derived from 5 with thiourea gave the desired benzotropolone, i.e., 6-hvdroxy-5H-benzocyclohepten-5-one (11), in high yield (Scheme 1). On the other hand, the endoperoxide 16 derived from the ethyl carboxylate derivat...
Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde
Tanyeli, Cihangir; ERDEM, Mine; ÇAKIR, Esen; KESKİN, Eda (Elsevier BV, 2007-09-27)
The asymmetric synthesis of cis-1,4-aminoalcohols with norbornene and norbornane backbone was performed starting with (2S, 3R)-(-)-cis-hemiester 1 (98% ee). Chemoselective amination with HMPTA followed by Grignard reactions and subsequent LAH reductions afforded compounds 5a-d. cis-Hemiester 1 was also transformed into chiral ligands 7a-f and 9a-d with the DCC coupling method followed by LAH reduction using acyclic, heterocyclic amines and various aniline derivatives and p-toluenesulfonamide, respectively. ...
Regioselective Synthesis of the 5,6-Dihydro-4H-furo[2,3-c]pyrrol-4-one Skeleton: A New Class of Compounds
Koza, Gani; Karahan, Emrah; Balcı, Metin (Wiley, 2010-01-01)
We hereby report the first preparation of the 5,6-dihydro-4H-furo[2.3-c]pyrrol-4-one (3) and its derivatives starting from methyl 3-(methoxycarbonyl)furnan-2-acetate (8). The ester functionality connected to the methylene group was regiospecifically converted to the desired monohydrazide 9. Conversion of 9 into the acyl azide In followed by Curtius rearrangement gave the corresponding isocyanate derivative 11 (Scheme 2). Reaction of 11 with different nucleophiles produced urethane and urea derivatives (Sche...
Citation Formats
O. De Lucchi, A. Dastan, A. Altundas, F. Fabris, and M. Balcı, “Cyclotrimerization of ‘Oxabenzonorbornadiene’: Synthesis of syn- and anti-5,6,11,12,17,18-hexahydro-5,18:6,11 : 12,17-triepoxytrinaphthylene,” HELVETICA CHIMICA ACTA, pp. 2364–2367, 2004, Accessed: 00, 2020. [Online]. Available: