C -Nucleosides and Related Compounds. IV. The Synthesis and Chemistry of D,L-2,5-Anhydroallose Derivatives

1975 ◽  
Vol 53 (1) ◽  
pp. 131-137 ◽  
Author(s):  
George Just ◽  
Alain Martel ◽  
Karl Grozinger ◽  
Mohabir Ramjeesingh
Keyword(s):  
Wittig Reaction ◽  
Diels Alder ◽  
Free Aldehyde ◽  
Related Compounds ◽  
Alder Adduct

Methyl β-nitroacrylate (1) reacted with furan to give the corresponding Diels–Alder adduct, which was converted to D,L-3,4-di-O-isopropylidene-2,5-anhydroallose (9) in a five-step sequence in 14% yield, based on 1. The conversion of 9 to its oxime, semicarbazone, and thiosemi-carbazone is described, as well as the synthesis of the free aldehyde 15, and of the Wittig reaction product 14.

C-Nucleosides and related compounds. VI. Carbocyclic analogues of C-nucleosides: synthesis and derivatives of some useful intermediates

1976 ◽  
Vol 54 (6) ◽  
pp. 849-860 ◽  
Author(s):  
George Just ◽  
Grant Reader ◽  
Bernadette Chalard-Faure
Keyword(s):  
Acrylic Acid ◽  
Wittig Reaction ◽  
Diels Alder ◽  
Reaction Products ◽  
Free Aldehyde ◽  
Derivatives Of ◽  
Related Compounds ◽  
Alder Adduct

The Diels–Alder adduct of cyclopentadiene and β-bromo acrylic acid 1 was converted to D,L-exo-6,7-(dihydroxy-di-O-isopropylidene)-2-hydroxy-3-oxabicyclo[3.2.1]octane (9) in an eight-step sequence and a 24% yield based on 1. Alternatively, the hemiacetal 9 was obtained in five steps and 22% yield from norbornadiene through the intermediate lactone 11. The thiosemicarbazone and semicarbazone of 9 were prepared. The synthesis of the free aldehyde 13 as well as that of the Wittig reaction products 12 and 19 are described.

C-Nucleosides and related compounds. XV. The synthesis of D,L-2′-epi-showdomycin and D,L-showdomycin

1980 ◽  
Vol 58 (19) ◽  
pp. 2024-2033 ◽  
Author(s):  
George Just ◽  
T. J. Liak ◽  
Mu-Ill Lim ◽  
Pierre Potvin ◽  
Youla S. Tsantrizos
Keyword(s):  
Diels Alder ◽  
Related Compounds ◽  
Alder Adduct

The conversion of the Diels–Alder adduct of methyl β-nitroacrylate with furan to the title compounds and to D,L-2,5-anhydroglucose derivatives is described.

C-Nucleosides and related compounds. XI. The synthesis of the 2-deoxy carbocyclic analogue of D,L-pyrazofurin A

1976 ◽  
Vol 54 (18) ◽  
pp. 2935-2939 ◽  
Author(s):  
George Just ◽  
Sunggak Kim
Keyword(s):  
Title Compound ◽  
Diels Alder ◽  
Related Compounds ◽  
Alder Adduct

The title compound bas been synthesized in an eleven-step sequence, starting from the known Diels–Alder adduct 7.

Reactions of N-3′-furylbenzamide with some dienophiles

1979 ◽  
Vol 57 (3) ◽  
pp. 314-317 ◽  
Author(s):  
John N. Bridson
Keyword(s):  
Double Bond ◽  
Maleic Anhydride ◽  
Methyl Acrylate ◽  
Diels Alder ◽  
First Case ◽  
Dimethyl Maleate ◽  
Related Compounds ◽  
Alder Adduct

N-3′-Furylbenzamide gives a conventional Diels–Alder adduct with maleic anhydride but with dimethyl maleate and methyl acrylate further reactions take place at the enamide grouping of the initially formed adducts. Compounds have been isolated in which molecules of an alcohol, used as solvent, or the starting furan have added to the double bond of the 1:1 adducts. In the first case unstable alkoxyamides are formed; in the second stable 2:1 adducts result from a novel uncatalysed addition to the double bond of the enamide. The stereochemistry of these and related compounds is discussed.

C-Nucleosides and related compounds. XIII. Synthesis of D,L-2′-deoxyshowdomycin (1d)

1977 ◽  
Vol 55 (16) ◽  
pp. 2993-2997 ◽  
Author(s):  
George Just ◽  
Mu-Ill Lim
Keyword(s):  
Title Compound ◽  
Diels Alder ◽  
Related Compounds ◽  
Alder Adduct

Starting from the Diels–Alder adduct of furan and methyl β-nitroacrylate, the synthesis of the title compound is described.

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