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The synthesis of trisporic acids

Creator:: Prisbylla, Michael Paul
Abstract:: A total synthesis of the fungal hormones, trisporic acids A and B, is described, starting from a -methyltetronic acid 34. A Robinson annelation of 34 with ethyl vinyl ketone affords the lactone 33. Treatment of 33 with N-bromosuccinimide gave 97, which was hydrolyzed to the lactol 103. The reaction of...
Resource Type:: Dissertation
Full Text:: THESIS OF Michael Paul Prisbylla for the degree of Doctor of Philosophy in Chemistry presented on July

Natural product synthesis via cyclobutanes : part I, Asymmetric synthesis of (+)-byssochlamic acid, part II, An approach to the nootropic agent huperzine A

Creator:: Kim, Jungchul
Abstract:: PART I. Asymmetric syntheses of both natural (+)- and nonnatural (-)-byssochlamic acid via a [2+2] photoaddition-cycloreversion strategy are described. X-ray crystallographic analysis of the cyclohexylamine salt 99 showed that the structure of the monomethyl ester 100 from esterase hydrolysis of 44 was originally misassigned as 56. The enantiomeric relationship of...
Resource Type:: Dissertation
Full Text:: methoxypyridine system via an azadiene Diels- Alder reaction were unsuccessful. However, intramolecular Michael

Studies towards the total synthesis of (-)-kendomycin

Creator:: Smits, Helmars
Abstract:: Studies towards the total synthesis of (−)-kendomycin (1), a bacterial metabolite with a unique molecular architecture and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediate 208, containing all of the carbon atoms of 1. A Dötz annulation between alkyne 122 and novel chromium carbenoid...
Resource Type:: Dissertation
Full Text:: the free diol underwent an intramolecular Michael addition to furnish tetrahydropyran 44 with high

Cis-2,5-diaminobicyclo[2.2.2]octane : a novel C₂-symmetric scaffold for asymmetric catalysis

Creator:: Shaw, Subrata
Abstract:: This thesis describes the development of a new enantioselective synthetic method employing chiral cis-2,5-diaminobicyclo[2.2.2]octane-based organometallic catalysts. The significance of this new method to organic synthesis is illustrated with preparation of enantioenriched products that are transformed to important pharmaceutical agents. Chapter 1 provides a brief historical overview of asymmetric catalysis, especially...
Resource Type:: Dissertation
Full Text:: sulfa-Michael addition (SMA) of thiols to acyclic a,(3- unsaturated ketones. I3-Thiaketones are

The isolation and structure of leptosphaerin : a metabolite of the marine ascomycete, Leptosphaeria oraemaris (Linder) and A synthesis of the marine toxin, 9-isocyanopupukeanane

Creator:: Schiehser, Guy Alan
Abstract:: The ethyl acetate extract of the culture filtrate of the marine Ascomycete, Leptosphaeria oraemaris (Linder) yielded a novel metabolite designated by the common name leptosphaerin. An x-ray crystallographic structure analysis was disproved by the synthesis of 3-acetoxy-S-(1,2-dihydroxyethyl)- 3-pyrrolin-2-one 1, starting with N,N-dibenzylhydroxylamine 47 and D-mannitol 44. Oxidation of 47 followed...
Resource Type:: Dissertation
Full Text:: ethyldiazoacetate to give 4-carboxyethyl-l-methoxy-5-methyltricyclo[5.1.0.03'5]octane 26. Acid catalyzed

Approaches toward the asymmetric synthesis of pillaromycin A

Creator:: Nolen, Ernest G.
Resource Type:: Dissertation
Full Text:: parallel sequence to the AB ring system of pillaromycinone was achieved from L-rhamnal. Glycolization and

Synthetic transformations of shikimic acid

Creator:: White, Edward D., III
Abstract:: Four strategies which involve synthetic elaboration of the shikimate nucleus are discussed. Methyl shikimate was differentially protected as the 3,4-0-cyclopentylidene ketal and as the 5- 0- tert- butyldiphenylsilyl ether. The methyl ester was then reduced with diisobutylaluminum hydride and the resulting allylic alcohol was oxidized to aldehyde 47 with pyridinium...
Resource Type:: Masters Thesis
Full Text:: McCrindle Synthesis of d,l-Shikimic Acid Schematic Diagram of a Retrosynthesis of Koumine Schematic

Total synthesis of indole alkaloids: pt. 1. Asymmetric synthesis of (-)-ibogamine. pt. 2. An approach toward the synthesis of koumine

Creator:: Choi, Younggi
Abstract:: PART I. The preparation of (-)-ibogamine (1) in fourteen steps from benzoquinone and in 10% overall yield is a powerful illustration of the value of the asymmetric Diels-Alder reaction as a starting point in a multistep synthesis. All four cycloadducts, 70, 77, 84 and 96, obtained with the (S)-BINOL-TiCl₂ complex...
Resource Type:: Dissertation
Full Text:: , Scott J. Kemp, Linda E. Keown, Jungchul Kim, Sung-kee Kim, Eric A. Korf, Christian L. Kranman, Punlop

Cyclization of olefinic β-ketoesters. An approach to the synthesis of aplysistatin

Creator:: Skeean, Richard William
Resource Type:: Dissertation
Full Text:: acknowledge the Nicholas L. Tartar Foundation for its financial aid during a portion of this work. Finally

Total synthesis of (-)-7-epicylindrospermopsin

Creator:: Hansen, Joshua D.
Abstract:: The first asymmetric synthesis of (-)-7-epicylindrospermopsin via intramolecular nitrone cycloaddition is described. The synthesis utilized a convergent approach to prepare the cycloaddition precursor 176, which was assembled by condensation of hydroxylamine 175 with aldehyde 145. Hydroxylamine 175 was synthesized from ethylene glycol (166) in seven steps. Aldehyde 145 was completed...
Resource Type:: Dissertation
Full Text:: inhibition exerted by cylindrospermopsin is still unclear. 7 Either l"glutamylcysteine synthetase or

ScholarsArchive@OSU

The synthesis of trisporic acids

Natural product synthesis via cyclobutanes : part I, Asymmetric synthesis of (+)-byssochlamic acid, part II, An approach to the nootropic agent huperzine A

Studies towards the total synthesis of (-)-kendomycin

Cis-2,5-diaminobicyclo[2.2.2]octane : a novel C₂-symmetric scaffold for asymmetric catalysis

The isolation and structure of leptosphaerin : a metabolite of the marine ascomycete, Leptosphaeria oraemaris (Linder) and A synthesis of the marine toxin, 9-isocyanopupukeanane

Approaches toward the asymmetric synthesis of pillaromycin A

Synthetic transformations of shikimic acid

Total synthesis of indole alkaloids: pt. 1. Asymmetric synthesis of (-)-ibogamine. pt. 2. An approach toward the synthesis of koumine

Cyclization of olefinic β-ketoesters. An approach to the synthesis of aplysistatin

Total synthesis of (-)-7-epicylindrospermopsin

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