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.

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.

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.

Synthesis of (±)-epiisopodophyllotoxin

1983 ◽  
Vol 61 (3) ◽  
pp. 573-575 ◽  
Author(s):  
Margaret B. Glinski ◽  
Tony Durst
Keyword(s):  
Title Compound ◽  
Dimethyl Fumarate ◽  
Dimethyl Acetal ◽  
Alder Reaction ◽  
Diels Alder ◽  
Carbon Skeleton ◽  
Diels Alder Reaction ◽  
Alder Adduct

The synthesis of (±)-epiisopodophyllotoxin commencing with 6-bromopiperonal dimethyl acetal is described. The carbon skeleton of isoepipodophyllotoxin was assembled via a Diels–Alder reaction between the hydroxyquinodimethane generated photochemically from 6-(3′,4′,5′-trimethoxybenzyl)-piperonal, obtained from the bromoacetal above, and dimethyl fumarate. This Diels–Alder adduct was converted in five steps into the title compound. The overall yield for the seven steps was 15%.

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. VIII. Synthesis of 5-(4′β-hydroxymethyl-2′β,3′α-dihydroxycyclopent-1′β-yl)-6-azauracil

1976 ◽  
Vol 54 (18) ◽  
pp. 2925-2934 ◽  
Author(s):  
G. Just ◽  
R. Ouellet
Keyword(s):  
Double Bond ◽  
Title Compound ◽  
Sodium Methoxide ◽  
Alder Reaction ◽  
Oxidative Cleavage ◽  
Diels Alder ◽  
Keto Ester ◽  
Diels Alder Reaction ◽  
Related Compounds

Starting from the Diels–Alder reaction of trans-β-bromoacrylic acid with cyclopentadiene, a synthesis of the substituted bicycloheptene 8 is described. The stereochemistry of the substituents is clearly defined. Oxidative cleavage of the double bond in the compound 8c afforded an acid keto ester 10 that was treated with thiosemicarbazide. Treatment of the resulting thiosemicarbazone 11 with sodium methoxide gave a 3-thioxo-1,2,4-triazine-5-one compound that was converted into the title compound.

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.

A Total Synthesis of Dimethyl 2,3-O-Isopropylidene-l-O-oxalyl-β-DL-ribo-hexofuran-5-ulosuronate

1975 ◽  
Vol 53 (18) ◽  
pp. 2701-2706 ◽  
Author(s):  
George Just ◽  
Karl Grozinger
Keyword(s):  
Total Synthesis ◽  
Title Compound ◽  
Catalytic Reduction ◽  
Major Product ◽  
Diels Alder ◽  
High Yield ◽  
Thermal Rearrangement ◽  
Dimethyl Acetylenedicarboxylate ◽  
Alder Adduct

The synthesis of the title compound 5 was accomplished by a high-yield thermal rearrangement of the ozonide (3) of dimethyl 5,6-O-isopropylidene-7-oxabicyclo[2.2.1]hept-2-ene-exo-5,6-diol-2,3-dicarboxylate (2a), which is obtained in 30% yield from the Diels–Alder adduct of furan and dimethyl acetylenedicarboxylate. Catalytic reduction of 5 gave methyl 2,3-O-iso-propylidene-β-DL-talofuranuronate (8) as the major product, accompanied by a small amount of the allo isomer 9.

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