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Synthesis of bicyclo[5.3.0]azulene derivatives.

(2010)Synthesis and Reactions of Bicyclo[1.1.0]butanes. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Synthesis of bicyclo[5.3.0]azulene derivatives

AB - Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin.

Synthesis of 2-Aza-bicyclo[2.1.1]hexanes as analogues of the anti-feedant 2, 4-methanoproline.

An enantioselective and catalytic method for the synthesis of bridgehead quaternary carbon containing bicyclo[3.3.1]nonanes is described. The intramolecular desymmetric arylation of α-disubstituted 1,3-diketones was achieved using a chiral Pd/PHOX complex. A variety of bridged cyclic molecules, common skeleton for polyprenylated acylphloroglucinols, were obtained in up to 84% yield with 86% ee.

Synthesis of 3-Aza-bicyclo[3.1.0]hexan-2-one …

Both enantiomers of 13-(E) and 13-(Z) isomers of 11-cis-locked bicyclo[5.1.0]octanyl retinal were prepared by an improved synthesis and incubated with bovine opsin. The synthesis also establishes the absolute configuration of the enantiomers. Only one of the enantiomers binds to opsin, thus showing the steric restrictions regarding the middle polyene moiety of the retinoid molecule; this is in sharp contrast to the known leniency of the ring moiety binding site of retinoids. However, although one enantiomer is incorporated into the pigment, the circular dichroic spectrum of the pigment incorporating the bound enantiomer yields only a very weak Cotton effect, showing that, once incorporated, the bicyclo[5.1.0]octanyl chromophore is flattened by the opsin binding site. The titled retinoid was synthesized for study of the absolute conformation of the retinal pigment in rhodopsin.

N2 - A new and advantageous synthesis of 2-endo-substituted-6-endo-(methylthio)bicyclo[2.2.1]heptanes, especially suitable for the preparation of such compounds with 2-endo-hydroxy and amino substituents, is presented. Also reported is the synthesis of the conformationally restricted methionine analogue (±)-2-endo-amino-6-endo-(methylthio)bicyclo[2.2.1]heptane-2-exo- carboxylic acid and its crystal and molecular structure determined by X-ray crystallographic techniques.

Synthesis of Bicyclo[4. n .1]alkanones - ResearchGate

T1 - A new synthesis of 2-substituted 6-endo-(methylthio)bicyclo[2.2.1]heptanes. Synthesis and crystal and molecular structure of a conformationally restricted methionine analogue

AB - A new and advantageous synthesis of 2-endo-substituted-6-endo-(methylthio)bicyclo[2.2.1]heptanes, especially suitable for the preparation of such compounds with 2-endo-hydroxy and amino substituents, is presented. Also reported is the synthesis of the conformationally restricted methionine analogue (±)-2-endo-amino-6-endo-(methylthio)bicyclo[2.2.1]heptane-2-exo- carboxylic acid and its crystal and molecular structure determined by X-ray crystallographic techniques.

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  • Synthesis of Bicyclo[3.3.0]octane-2,6-dione - …

    “Synthesis of 2-Aza-bicyclo[2.1.1]hexanes as Analogues of the Anti-feedant 2, 4-methanoproline.” In .

  • The Bicyclo[1.1.0]Butane Group (a) Synthesis

    “Synthesis of 2-Aza-bicyclo[2.1.1]hexanes as Analogues of the Anti-feedant 2, 4-methanoproline.” .

  • A versatile synthesis of bicyclo[2.2.2]octan-2-one derivatives

    T1 - Synthesis of a pericosine analogue with a bicyclo[2.2.2]octene skeleton

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AN IMPROVED SYNTHESIS OF BICYCLO[2,1,1]HEXANE …

A new and advantageous synthesis of 2-endo-substituted-6-endo-(methylthio)bicyclo[2.2.1]heptanes, especially suitable for the preparation of such compounds with 2-endo-hydroxy and amino substituents, is presented. Also reported is the synthesis of the conformationally restricted methionine analogue (±)-2-endo-amino-6-endo-(methylthio)bicyclo[2.2.1]heptane-2-exo- carboxylic acid and its crystal and molecular structure determined by X-ray crystallographic techniques.

Synthesis and reactivity of bicyclo[3.2.1]octanoid …

Carvone is a sustainable and readily available starting material for organic synthesis. Herein, we present the syntheses of various natural product scaffolds that rely on a novel benzannulation involving the α-methyl group (C-10) of carvone to afford a versatile tetralin. The utility of our synthetic approach is highlighted by its application to a short synthesis of the 3,4-atisane diterpenoid (−)-crotogoudin. The 13-step enantiospecific synthesis features a regioselective double oxidative dearomatization, a Diels–Alder cycloaddition with ethylene gas (to construct the bicyclo[2.2.2]octane framework), and a final acid-mediated lactonization. The versatility of this benzannulation strategy is demonstrated by its utility in the preparation of the carbon skeleton of -3,4-abietane diterpenoids using an intramolecular oxidative dearomatization.

Acid-catalyzed synthesis of bicyclo[3.n.1]alkenediones.

A new analogue of the antitumor pericosines possessing a bicyclo[2.2.2]octene skeleton has been synthesized from methyl gallate using oxidative dearomatization and regio- and diastereoselective Diels-Alder reaction as the key steps.

Nolting DD(1), Nickels M, Price R, Gore JC, Pham W

An enantioselective and catalytic method for the synthesis of bridgehead quaternary carbon containing bicyclo[3.3.1]nonanes is described. The intramolecular desymmetric arylation of α-disubstituted 1,3-diketones was achieved using a chiral Pd/PHOX complex. A variety of bridged cyclic molecules, common skeleton for polyprenylated acylphloroglucinols, were obtained in up to 84% yield with 86% ee.

This item was digitized from a paper original and/or a microfilm copy

T1 - Synthesis and structural verification of novel olefinic derivatives of bicyclo[2.2.2]octane. Intermediates in the synthesis of bridged morphinan-like compounds

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