scholarly journals On the structure of the adduct from the aluminium chloride catalyzed Diels–Alder reaction of 2-methyl-2-cyclohexenone with isoprene

1984 ◽  
Vol 62 (3) ◽  
pp. 481-483 ◽  
Author(s):  
Jagabandhu Das ◽  
Zdenek Valenta ◽  
Hsing-Jang Liu ◽  
Teng Ko Ngooi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Aluminium Chloride ◽  
Keto Ester ◽  
Diels Alder Reaction

An unequivocal correlation of keto ester 3 and the adduct obtained from the aluminium chloride catalyzed Diels–Alder reaction of 2-methyl-2-cyclohexenone with isoprene confirms the structure of the adduct to be 2.

The synthesis of trisubstituted cyclopentadienes and their reactivity in the intramolecular Diels–Alder reaction

1984 ◽  
Vol 62 (1) ◽  
pp. 121-127 ◽  
Author(s):  
Sandra J. Alward ◽  
Alex G. Fallis
Keyword(s):  
Adverse Effect ◽  
Alder Reaction ◽  
Diels Alder ◽  
Keto Ester ◽  
Diels Alder Reaction ◽  
General Method

The intramolecular Diels–Alder reactivity of several trisubstituted cyclopentadienes is described and a general method for their preparation reported. In general, sidechain keto-ester functionality has an adverse effect on these internal cycloadditions.

Total synthesis of androstanes

1979 ◽  
Vol 57 (24) ◽  
pp. 3356-3358 ◽  
Author(s):  
Masatoshi Kakushima ◽  
Jagabandhu Das ◽  
Gary R. Reid ◽  
Peter S. White ◽  
Zdenek Valenta
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Keto Ester ◽  
Diels Alder Reaction ◽  
Androstane Derivatives

A total synthesis of androstane derivatives is described. The desired configuration at C8 and at C13 is achieved in a ring C forming SnCl4-catalyzed Diels–Alder reaction. The preparation of methyl Z-2-methyl-4-oxo-2-pentenoate and the cyclization of a keto ester to a steroid 15,17-dione are also reported.

Total synthesis of amphilectane-type diterpenoids: (±)-8,15-diisocyano-11(20)-amphilectene

1993 ◽  
Vol 71 (9) ◽  
pp. 1484-1494 ◽  
Author(s):  
Edward Piers ◽  
Montse Llinas-Brunet ◽  
Renata M. Oballa
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Allylic Oxidation ◽  
Keto Ester ◽  
Efficient Transformation ◽  
Diels Alder Reaction ◽  
Product Mixture

A total synthesis of the structurally novel, antimicrobial diterpenoid (±)-8,15-diisocyano-11(20)-amphilectene (2) is described. Alkylation of 2-methoxycarbonyl-3-methylcyclohexanone (13) with (E)-1-(tert-butyldimethylsiloxy)-6-iodo-3-(trimethylstannyl)-2-hexene (14) provided, stereoselectively, the functionalized keto ester 15, which was converted efficiently into the diene 17. Diels–Alder reaction of 17 with acrolein, followed by base-catalyzed equilibration of the resultant product mixture, gave the aldehydes 19 (58%) and 20 (29%). Allylic oxidation of the alkene 24 (derived from 19) afforded the enone 25. Reduction (Na, NH3, t-BuOH) of 25 gave 28, which was converted, via a sequence of eight synthetic steps, into the diacid 45. Efficient transformation of the carboxyl functions of 45 into isonitrile groups completed the synthesis of (±)-2.

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.

The Diels-Alder Reaction of 2-Ethenyl-1,4-Benzodioxin: A New and Simple Synthesis of Bisaryl Ethers

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Simple Synthesis ◽  
Diels Alder Reaction

The intermolecular anthracene-transfer in a regiospecific antipodal C60 difunctionalization

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz
Keyword(s):  
Noncovalent Interactions ◽  
Interaction Model ◽  
Alder Reaction ◽  
Diels Alder ◽  
Stacking Interactions ◽  
Pi Stacking ◽  
Diels Alder Reaction ◽  
Double Decker ◽  
Anthracene Molecule ◽  
New Strategies

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>

Natural Products Biosynthesis Involving a Putative Diels-Alder Reaction

2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction
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