111080-27-4Relevant articles and documents
Polypropionates from 7-oxanorbornene derivatives. A stereoselective and divergent synthesis of fragments with four contiguous chiral centers
Acena, Jose Luis,Arjona, Odon,Leon, Marisa,Plumet, Joaquin
, p. 8957 - 8960 (1996)
The epimeric stereotetrads 12 and 14 have been prepared starting from the Diels-Alder endo adduct of furan and acrylic acid. The key steps of the route were the alkylative cleavage of the oxygen bridge and the transformation of the resulting cyclic vinyl
Norbornenes in inverse electron-demand diels-alder reactions
Vrabel, Milan,Koelle, Patrick,Brunner, Korbinian M.,Gattner, Michael J.,Lopez-Carrillo, Veronica,De Vivie-Riedle, Regina,Carell, Thomas
, p. 13309 - 13312 (2013)
Significant differences in the reactivity of norbornene derivatives in the inverse electron-demand Diels-Alder reaction with tetrazines were revealed by kinetic studies. Substantial rate enhancement for the exo norbornene isomers was observed (see scheme). Quantum-chemical calculations were used to rationalize and support the observed experimental data. Copyright
COMPOUNDS AND USES THEREOF FOR THE MODULATION OF HEMOGLOBIN
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Paragraph 0336, (2015/05/26)
Provide herein are compounds and pharmaceutical compositions suitable as modulators of hemoglobin, methods and intermediates for their preparation, and methods for their use in treating disorders mediated by hemoglobin and disorders that would benefit from tissue and/or cellular oxygenation.
Organocatalytic asymmetric Diels-Alder reaction of furan under high pressure
Mimoto, Akiko,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
scheme or table, p. 799 - 804 (2010/10/05)
A new method for the asymmetric Diels-Alder reaction between furan and acrolein has been developed through the combined use of chiral organocatalysts and high pressure (yield up to 91%; endo-adduct up to 19% ee, exo-adduct up to 26% ee).
Synthesis of novel carbocyclic nucleoside analogues derived from 7-oxabicyclo[2.2.1]heptane-2-methanol
Hrebabecky, Hubert,Dracinsky, Martin,De Palma, Armando M.,Neyts, Johan,Holy, Antonin
experimental part, p. 487 - 502 (2009/07/11)
Hydroboration of [(lR*,2R*,4R*)-7-oxabicyclo[2.2.1]hept- 5-en-2-yl]methyl benzoate (5), which was prepared by Diels-Alder reaction of furan with acrolein and subsequent reduction and benzoylation of the Diels-Alder product, afforded [(lR*,2S*,4S*,6S*)-6-h
The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo [3.2.1]oct-6-en-2-one to soft electrophiles
Fattori, Daniela,Henry, Sylvie,Vogel, Pierre
, p. 1649 - 1664 (2007/10/02)
Nitrosation of 7-oxabicyclo[2.2.1]hept-5-en-2-exo-ylmethyl amine (20) gave 7-oxabicydo[2.2.1]hept-5-en-2-exo-methanol (22) whereas 7-oxabicyclo[2.2.1]hept-5-en-2-endo-ylmethylamine (21) afforded a 1:1 mixture of 7-oxabicydo[3.2.1]oct-6-en-2-ols (23) and 8-oxabicydo[3.2.1]oct-3-en-2-ols (24). Nitrosations of 2-exo- (28) and 2-endo-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ol (29) gave mixtures of 8-oxabicydo[3.2.1]oct-6-en-2-one (25) and 8-oxabicydo[3.2.1]oct-6-en-3-one (37). The preference for the C(3) methylene group migration giving 25 was the best (12:1) in the case of the 2-endo-aminomethyl alcohol 29. Compared with the nitrosations of bicydo[2.2.1]heptane analogues, the 7-oxa bridge in 28 and 29 enhances the preference for the C(3) methylene group migration vs. the C(1) methine group migration. The Tiffeneau-Demjanov one-carbon ring enlargement reactions of 2-exo-aminomethyl-7-oxabicyclo[2.2.1]hepta-2-endo-ol (30). 2-exo-aminomethyl-5-chloro (32) and 2-exo-aminomethyl-6-chloro-7-oxabicyclo[2.2.1]hept-5-en-endo-ol (33) are also reported. Under kinetically controlled conditions, 8-oxabicydo[3.2.1]oct-6-en-2-one (25) adds to electrophiles EX=PhSeCl, PhSeBr. 2,4-(NO)2C6H3SCl with high stereo- and regioselectivity giving the corresponding 8-oxabicyclo [3.2.1]-octan-2-ones where E substitutes the exo position of C(6) and X the exo position of C(7).
Synthesis of Amino-5a-carba-deoxyhexopyranoses from 2(3)-Acetoxy-5-acetoxymethyl-3(2)-p-toluenesulfonamido-7-oxabicycloheptanes
Ogawa, Seiichiro,Tsunoda, Hidetoshi,Yoshikawa, Masaru,Uemura, Masaki,Orihara, Masaru
, p. 629 - 636 (2007/10/02)
cis-Hydroxyamination of endo-2-acetoxymethyl-7-oxabicyclohept-5-ene (1) under Sharpless condition affords two positional isomers 3 and 7 of 5-endo-acetoxymethyl-2(3)-exo-hydroxy-3(2)-exo-p-toluenesulfonamido-7-oxabicycloheptanes.Cleavage of
Regioselective electrophilic additions to 2-alkoxy- and 2-alkoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene derivatives
Arjona,Fernandez De La Pradilla,Pita-Romero,Plumet,Viso
, p. 8199 - 8206 (2007/10/02)
The influence of the stereochemistry at C-2 on the selectivity of the reaction between PhSeBr and 2-alkoxymethyl substituted oxanorbornenes has been studied. All endo isomers displayed complete regio- and stereocontrol with incorporation of the electrophi
Synthetic Studies of Diels-Alder Adduct of Furan. Formal Total Synthesis of (+/-)-Avenaciolide
Kotsuki, Hiyoshizo,Ohnishi, Hiroyuki,Akitomo, Yasuhiro,Ochi, Masamitsu
, p. 3881 - 3884 (2007/10/02)
The endo-Diels-Alder adduct of furan with methyl acrylate was transformed into a bis-γ-lactone derivative which is a well-known precursor for the synthesis of (+/-)-avenaciolide.The route involves 13 steps and the overall yield was 17.9percent.
