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Full-Text Articles in Organic Chemistry

Enantiospecific Stereospecific Strategy For The Total Synthesis Of Sarpagine And Macroline Related Oxindole Alkaloids: First Total Synthesis Of Affinisine Oxindole, Isoalstonisine, Alstofoline, Macrogentine, N(1)-Demethylalstonisine, Alstonoxine A And Second Generation Synthesis Of Alstonisine, German Oscar Fonseca Cabrera Aug 2015

Enantiospecific Stereospecific Strategy For The Total Synthesis Of Sarpagine And Macroline Related Oxindole Alkaloids: First Total Synthesis Of Affinisine Oxindole, Isoalstonisine, Alstofoline, Macrogentine, N(1)-Demethylalstonisine, Alstonoxine A And Second Generation Synthesis Of Alstonisine, German Oscar Fonseca Cabrera

Theses and Dissertations

The (7R)-sarpagine/macroline related oxindole alkaloids (-)-isoalstonisine (27) and (-)-macrogentine (31) together with the (7S)-sarpagine/macroline related oxindole alkaloids (-)-affinisine oxindole (24), (-)-alstonoxine A (19), (+)-alstonisine (8, second generation total synthesis), (+)-Na-demethylalstonisine (17) and (+)-alstofoline (18) were concisely synthesized during these studies.

These oxindole alkaloids were isolated from plants of the genus Alstonia which is characterized by the preponderance of sarpagine/macroline-type indole and oxindole alkaloids. Plants that belong to this genus are mainly distributed over tropical regions of Central America, Africa, and Asia where they are used locally in traditional medicine, for example, in the treatment of ...


Total Synthesis Of (-)-Calyciphylline N, Artem Shvartsbart Jan 2014

Total Synthesis Of (-)-Calyciphylline N, Artem Shvartsbart

Publicly Accessible Penn Dissertations

The dissertation herein describes the first total synthesis of the complex Daphniphyllum alkaloid, (-)-calyciphylline N. This alkaloid was chosen as the target in our synthetic program due its unprecedented structure, the inherent challenges associated with its synthesis, and limited reports of synthetic studies towards members of this family of natural products. An initial unsuccessful approach is discussed, followed by a revised, ultimately successful approach. Highlights of the synthesis include a substrate controlled, intramolecular Diels-Alder reaction to build the bicyclo[2.2.2]octane core and set four contiguous stereocenters, a transannular enolate alkylation to secure ring D, a highly efficient ...


Synthetic And Biosynthetic Approaches To Cherylline And Related Compounds , Richard Duane Shaffer Jan 1972

Synthetic And Biosynthetic Approaches To Cherylline And Related Compounds , Richard Duane Shaffer

Retrospective Theses and Dissertations

No abstract provided.


The Structures And Reactions Of Four New 5,10b-Ethanophenanthridine Alkaloids , Michael Ray Slabaugh Jan 1970

The Structures And Reactions Of Four New 5,10b-Ethanophenanthridine Alkaloids , Michael Ray Slabaugh

Retrospective Theses and Dissertations

No abstract provided.


The Biosynthesis Of Lycorenine, Narciclasine, And Dimethoxy Analogues Of Lycorine , Russel D. Harken Jan 1970

The Biosynthesis Of Lycorenine, Narciclasine, And Dimethoxy Analogues Of Lycorine , Russel D. Harken

Retrospective Theses and Dissertations

No abstract provided.


The Chemistry Of Pretazettine And Related Compounds , David Tiffany Bailey Jan 1968

The Chemistry Of Pretazettine And Related Compounds , David Tiffany Bailey

Retrospective Theses and Dissertations

No abstract provided.


The Mass Spectra Of Montanine- And Galanthamine-Type Alkaloids: The Structures Of Pancracine And Habranthine , Costello Leon Brown Jan 1968

The Mass Spectra Of Montanine- And Galanthamine-Type Alkaloids: The Structures Of Pancracine And Habranthine , Costello Leon Brown

Retrospective Theses and Dissertations

No abstract provided.


The Incorporation Of 14c-Labeled [Beta]-Phenylethylamine Derivatives And 3h-Vittatine Into Amaryllidaceae Alkaloids , Allen Irwin Feinstein Jan 1967

The Incorporation Of 14c-Labeled [Beta]-Phenylethylamine Derivatives And 3h-Vittatine Into Amaryllidaceae Alkaloids , Allen Irwin Feinstein

Retrospective Theses and Dissertations

No abstract provided.


Dichroism And Dispersion Studies Of The Optically Active Aromatic Chromophore , Gerald George Deangelis Jan 1966

Dichroism And Dispersion Studies Of The Optically Active Aromatic Chromophore , Gerald George Deangelis

Retrospective Theses and Dissertations

No abstract provided.


The Chemistry Of 6-Hydroxycrinamine And Related Compounds , Charles Franklin Murphy Jan 1966

The Chemistry Of 6-Hydroxycrinamine And Related Compounds , Charles Franklin Murphy

Retrospective Theses and Dissertations

No abstract provided.


Derivatives Of Aromatic Resin Acids , Richard William James Carney Jan 1962

Derivatives Of Aromatic Resin Acids , Richard William James Carney

Retrospective Theses and Dissertations

No abstract provided.


Chemical Transformations In The Field Of Indole Alkaloids , Robert Lin Sung Amai Jan 1962

Chemical Transformations In The Field Of Indole Alkaloids , Robert Lin Sung Amai

Retrospective Theses and Dissertations

No abstract provided.


Syntheses Of Tryptamine Bases , Frank James Kilzer Jan 1962

Syntheses Of Tryptamine Bases , Frank James Kilzer

Retrospective Theses and Dissertations

No abstract provided.


Structure Studies On Gelsemine , John Holmes Hansen Jan 1960

Structure Studies On Gelsemine , John Holmes Hansen

Retrospective Theses and Dissertations

No abstract provided.


Dehydrogenation Studies In The Field Of Indole Alkaloids , Dilip Kumar Roychaudhuri Jan 1957

Dehydrogenation Studies In The Field Of Indole Alkaloids , Dilip Kumar Roychaudhuri

Retrospective Theses and Dissertations

Two methods of dehydrogenation have been used for the oxidation of variously ring E-substituted yohimbine- and ajmalicine-type indole alkaloids;The first method, palladium-maleic acid dehydrogenation, produces ring C tetradehydro compounds and can be used for differentiating pseudo compounds from epiallo compounds. The second method, mercuric acetate oxidation, produces 3-dehydro compounds;By the use of the first method the stereochemistry of several indole alkaloids was elucidated;Infrared spectra in the C-H stretching region (3.4--3.7mu) have been used for differentiating between C3 epimers of indole alkaloids;Structures were proposed for several new compounds derived by oxidation or reduction of indole ...