Synthetic approaches to phorbols via the intramolecular Diels–Alder reaction of furans: influence of the dienophile upon the stereochemical control

1990 ◽  
pp. 608-610 ◽  
Author(s):  
Laurence M. Harwood ◽  
Brian Jackson ◽  
Geraint Jones ◽  
Keith Prout ◽  
Royston M. Thomas ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Stereochemical Control ◽  
Diels Alder Reaction ◽  
Synthetic Approaches

Synthetic Approaches towards [1]Benzopyrano [4,3-b]Thieno[2,3-e]Pyridines via Intramolecular Diels-Alder Reactions of 1,2,4-Triazines

2002 ◽  
Vol 2002 (2) ◽  
pp. 60-61 ◽  
Author(s):  
Yehia A. Ibrahim ◽  
Balkis Al-Saleh
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Synthetic Approaches

Efficient syntheses are reported of [1]benzopyrano[4,3-b]thieno[2,3-e]pyridines (20), by the application of an intramolecular Diels–Alder reaction employing the intermediate appropriately designed functionalised thieno [3,2-e][1,2,4]triazines.

scholarly journals Synthetic approaches to haplophytine. 2. Synthesis of 4-methylamino-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)butan-1-one

1983 ◽  
Vol 61 (6) ◽  
pp. 1126-1131 ◽  
Author(s):  
David Aaron Schwartz ◽  
Peter Yates
Keyword(s):  
Furan Ring ◽  
Alder Reaction ◽  
Diels Alder ◽  
Acid Moiety ◽  
Diels Alder Reaction ◽  
Synthetic Approaches

Approaches to the synthesis of compounds related to the 7-aryl-7-[3-(1-hydroxy-2-aminophenyl)]-9-methylamino-5,6-dioxononanoic acid moiety (3) of the alkaloid haplophytine and its dihydrobromide are described. Treatment of the dianion of phenyl (o-pivaloylamidophenyl)methane with 2-furancarboxaldehyde followed by oxidation of the resulting alcohol gives 1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)ethanone (14). This on allylation gives 1-allyloxy-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)ethene (20), which on being heated at 80–95 °C undergoes an intramolecular Diels–Alder reaction. Heating the resulting product or 20 at 165 °C converts them to the C-allylation product of 14, 1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)pent-4-en-1-one (22). Oxidation of 22 gives 4-(2-furoyl)-1,2,3,4-tetrahydro-4-phenyl-1-pivaloyl-2-quinolinol, which on Borch reduction gives 4-methylamino-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)butan-1-one (24) and 2-(2-furanyl)-1-methyl-3-phenyl-3-(2-pivaloylamidophenyl)pyrrolidine. Compound 24 is a potential advanced intermediate for the synthesis of compounds related to 3. Experiments directed to the incorporation of a methoxyl or methylthio substituent at the C-5 position of the furan ring of 24 are also described.

ChemInform Abstract: Synthetic Approaches Towards Phorbols via the Ultra-High-Pressure Mediated Intramolecular Diels-Alder Reaction of Furans (IMDAF): Effect of Furan Substitution.

ChemInform ◽  
2010 ◽  
Vol 30 (34) ◽  
pp. no-no
Author(s):  
Angela C. Brickwood ◽  
Michael G. B. Drew ◽  
Laurence M. Harwood ◽  
Tsutomu Ishikawa ◽  
Pierre Marais ◽  
...  
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ultra High Pressure ◽  
Diels Alder Reaction ◽  
Synthetic Approaches

Stereochemical control by an allylic substitutent of an acyclic dienophile in the Diels-Alder reaction

1982 ◽  
Vol 104 (4) ◽  
pp. 1106-1107 ◽  
Author(s):  
Richard W. Franck ◽  
Thomas V. John ◽  
Kazimierz Olejniczak ◽  
John F. Blount
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Stereochemical Control ◽  
Diels Alder Reaction
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