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.

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%.

The Two-step Synthesis and Crystal and Molecular Structure of Tetracyclo[6.4.0.02,11.04,9]dodec-6-ene-3,10-dione

1975 ◽  
Vol 53 (14) ◽  
pp. 2068-2075 ◽  
Author(s):  
Yuen-Mui Ngan ◽  
Steven J. Rettig ◽  
John R. Scheffer ◽  
James Trotter
Keyword(s):  
Crystal And Molecular Structure ◽  
Direct Methods ◽  
Membered Ring ◽  
Diels Alder ◽  
High Yield ◽  
Side Chain ◽  
X Ray ◽  
Long Wavelength ◽  
Vinyl Group ◽  
Alder Adduct

The photochemistry of the trans-1,3,5-hexatriene-p-benzoquinone Diels–Alder adduct has been investigated. Irradiation of this material in its long wavelength n → π* absorption band leads to a single photoproduct in high yield. A single crystal X-ray structure determination shows this product to be tetracyclo[6.4.0.02,11.04,9]dodec-6-ene-3,10-dione, the result of a novel regiospecific intramolecular 2 + 2 photoaddition between the side chain vinyl group and the enedione double bond. Crystals of tetracyclo[6.4.0.02,11.04,9]dodec-6-ene-3,10-dione are monoclinic, a = 7.5290(7), b = 19.072(1), c = 6.7237(4) Å, β = 107.918(6) °, Z = 4, space group P21/n. The structure was solved by direct methods and was refined by full-matrix least-squares procedures to a final R of 0.041 for 1603 reflections with I ≥ 3σ(I). The structure consists of well-separated molecular units. Bond distances are: C=O, 1.216 and 1.219(2), C=C, 1.318(2), mean C(sp3)—C(sp2), 1.508, mean C(sp3)—C(sp3), 1.560 in the four-membered ring and 1.544 elsewhere, mean C(sp3)—H, 0.99, and mean C(sp2)—H, 0.95 Å. Bond distances between nonhy drogen atoms have been corrected for thermal motion. A possible rationalization for the observed photoprocess is discussed in terms of conformational and radical stability effects.

scholarly journals Cover Picture: Total Synthesis Confirms Laetirobin as a Formal Diels-Alder Adduct (Chem. Asian J. 2/2010)

2010 ◽  
Vol 5 (2) ◽  
pp. 185-185
Author(s):  
Oliver Simon ◽  
Bastien Reux ◽  
James J. La Clair ◽  
Martin J. Lear
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Alder Adduct

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.

scholarly journals Diels-Alder Additions to 2,2’-Biaceanthrylene

2021 ◽  
Author(s):  
Yachu Du ◽  
Kyle Plunkett
Keyword(s):  
Polycyclic Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbon ◽  
Photophysical Properties ◽  
Major Product ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Polycyclic Aromatic ◽  
Single Addition ◽  
Quinone Derivative

A series of Diels-Alder reactions between the diene 2,2’-biaceanthylene and several dienophiles is presented. The diene is a cyclopenta-fused polycyclic aromatic hydrocarbon with anthracene units linked by two cyclopentene rings. Depending on the dienophile, the major product was the result of a single addition (dimethyl acetylenedicarboxylate) or double addition (quinone, benzyne) to the diene. Single crystal X-ray analysis of the quinone-derivative shows a propeller-like structure composed of mixed enantiomers. The synthesis and photophysical properties of these compounds is presented.<br>

Total Synthesis Confirms Laetirobin as a Formal Diels-Alder Adduct

2010 ◽  
Vol 5 (2) ◽  
pp. 342-351 ◽  
Author(s):  
Oliver Simon ◽  
Bastien Reux ◽  
James J. La Clair ◽  
Martin J. Lear
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Alder Adduct

Annelated furans. XI. The reactions of 2-vinylfurans with acetylenic esters

1973 ◽  
Vol 26 (5) ◽  
pp. 1059 ◽  
Author(s):  
WJ Davidson ◽  
JA Elix
Keyword(s):  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
Acetylenic Ester ◽  
Acetylenic Esters ◽  
Methyl Propiolate ◽  
Diene System ◽  
Alder Adduct ◽  
Ene Addition

In general dimethyl acetylenedicarboxylate and methyl propiolate have been found to react with 2-vinylfurans to give the corresponding dimethyl benzofuran-4,5-di-carboxylates and methyl benzofuran-4- carboxylates respectively. In several instances dimethyl acetylenedicarboxylate did not react exclusively with the exocyclic diene system of the 2-vinylfuran and here the corresponding dimethyl 3,6-epoxy-3-vinyl-3,6-dihydrophthalates were obtained by Diels-Alder addition to the furanoid diene system. At 80� 2-vinylfuran and dimethyl acetylenedicarboxylate formed the 1 : 2 adduct (11), the formation of which can be interpreted as involving an ene addition of a second mole of the acetylenic ester to the initially formed Diels-Alder adduct.

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