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.

Diels-Alder Reaction of Ni(II) β-Vinyl-meso-tetraphenylporphyrin; A General Method for Synthesis of Functionalized Porphyrins

Synlett ◽  
2000 ◽  
Vol 2000 (2) ◽  
pp. 233-235 ◽  
Author(s):  
Kiyoshi Matsumoto ◽  
Shinya Kimura ◽  
Takuya Morishita ◽  
Yukihiro Misumi ◽  
Naoto Hayashi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
General Method

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.

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.

ChemInform Abstract: Diels-Alder Reaction of Ni(II) β-Vinyl-meso-tetraphenylporphyrin: A General Method for Synthesis of Functionalized Porphyrins.

ChemInform ◽  
2010 ◽  
Vol 31 (20) ◽  
pp. no-no
Author(s):  
Kiyoshi Matsumoto ◽  
Shinya Kimura ◽  
Takuya Morishita ◽  
Yukihiro Misumi ◽  
Naoto Hayashi
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
General Method

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.

scholarly journals The effect of Lewis acids on the intramolecular Diels–Alder reaction of the furan diene

1992 ◽  
Vol 70 (12) ◽  
pp. 2929-2947 ◽  
Author(s):  
Christine Rogers ◽  
Brian A. Keay
Keyword(s):  
Carbon Atom ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Oxygen Bridge ◽  
Excellent Yield ◽  
Diels Alder Reaction ◽  
Alkyl Groups ◽  
General Method

A general method is described for effecting the intramolecular Diels–Alder reaction of the furan diene in which the side arm connecting the diene to the dienophile contains four carbon atoms. The use of 1.1 equivalents of methylaluminum dichloride at −78 °C for 2–8 h shifts the Diels–Alder equilibrium towards the products and provides the oxatricyclo adducts in good to excellent yield. Catalytic quantities of methylaluminum dichloride (10 mol%) provided a higher quantity of adduct than excess Lewis acid when the enone was substituted with alkyl groups. The scope was extended to include a precursor containing a five carbon atom side arm, and two examples containing acetylenic dienophiles that were activated by a carbonyl moiety on the side arm. Precursors having a four carbon atom side arm provided only oxatricyclo adducts having the side arm syn to the oxygen bridge. The assignment of the stereochemistry of the oxatricyclo adducts is discussed in detail.

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