Index Catalog // ScholarsArchive@OSU

Studies toward the total synthesis of sanglifehrin A

Creator:: Suttisintong, Khomson
Abstract:: Studies toward synthesis of subunits of sanglifehrin A, an immunosuppressant featuring a highly substituted [5,5]-spirolactam moiety as well as a 22-membered macrocycle are described. The macrolactone contains a peptidic backbone characterized by an unusual [beta]-substituted (S)-piperazic acid and (S)-m-hydroxyphenylalanine units. These studies resulted in the synthesis of advanced intermediate 358...
Resource Type:: Dissertation
Full Text:: synthesis of (S)-m- hydroxyphenylalanine derivative 244. Assembly of 244, piperazic acid 113 and L- valine

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

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

Intramolecular diels-alder cycloadditions of citraconic and mesaconic esters ; Studies on the synthesis of the northwest and southeast segments of boromycin

Creator:: Sheldon, Bernard Gale
Resource Type:: Dissertation
Full Text:: of the methyl ester 98, with diisobutyl- aluminum hydride to the acetal 99, exo-l-endo-10-dimethy1

Synthetic studies on necic acids of pyrrolizidine alkaloids

Creator:: Lee, Nadine Chauyi
Resource Type:: Dissertation
Full Text:: 6 R cs,L H-9 .,0 R N .:i 0 0 + Nu-, Nu-2 H+ Figure 1.2. Mechanism of

Synthesis of epothilones and epothilone analogues

Creator:: Sundermann, Kurt F.
Abstract:: A convergent synthesis of epothilone B that generates all seven of its asymmetric centers in a completely stereoselective fashion has been completed. Key reactions include an anti-Felkin aldol condensation to set the C6 and C7 stereochemistry, a directed α-hydroxylation to install the C15 (S)-hydroxyl substituent, and a Wittig condensation to...
Resource Type:: Dissertation
Full Text:: Epothilone B10 (11) NtS.OH Epothilone G1 (12), R = H Epothilorie G2 (13), R Me L/,SS0H Epothitone H1 (14

Synthetic studies on marine natural products : I. Stereoselective synthesis of E,Z-1,3-Dienes by tandem nucleophilic addition to a dienylphosphonium salt followed by Wittig reaction. II. Synthesis of cyclopropyl oxylipins by a cation mediated carbocyclization

Creator:: Jensen, Mark S.
Resource Type:: Dissertation
Full Text:: spectroscopy. The National Science Foundation and the N. L. Tartar Foundation are acknowledged for

Studies toward the total synthesis of phorboxazole A

Creator:: Kuntiyong, Punlop
Abstract:: Studies toward the total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, were conducted and resulted in a route to an advanced intermediate, C4-C32, for this purpose. A key feature of our approach is the stereoselective synthesis of two cis-2,6-disubstituted tetrahydropyrans present in the macrolide portion of...
Resource Type:: Dissertation
Full Text:: on studies toward the total synthesis of phorboxazole A. Dr. Christian L. Kranemann, a former

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:: . Skold for his most helpful suggestions. I would like to acknowledge the Nicholas L. Tartar Foundation

Chiral synthesis of monic acid C

Creator:: Theramongkol, Parinya
Abstract:: Bromoalkoxylation of dihydropyran with bromine and 1-borneol, followed by dehydrobromination and epoxidation, afforded trans-2-1- bornyloxy-3,4-epoxytetrahydropyran as a major product. This was treated with sodium phenylselenide to give a 1:1 mixture of (2R,3R,4R)- 2-1-bornyloxy-3-hydroxy-4-phenylselenotetrahydropyran and its (2S,3S, 4S) diastereomer. Elimination of the selenoxide, derived from oxidation of the former with hydrogen...
Resource Type:: Dissertation
Full Text:: Side Chain of L-Isoleucine. 6 3. Retrosynthetic Plan. 20 4. Epoxide Ring Opening by Selenide Anion

ScholarsArchive@OSU

Studies toward the total synthesis of sanglifehrin A

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

Total synthesis of (-)-7-epicylindrospermopsin

Intramolecular diels-alder cycloadditions of citraconic and mesaconic esters ; Studies on the synthesis of the northwest and southeast segments of boromycin

Synthetic studies on necic acids of pyrrolizidine alkaloids

Synthesis of epothilones and epothilone analogues

Synthetic studies on marine natural products : I. Stereoselective synthesis of E,Z-1,3-Dienes by tandem nucleophilic addition to a dienylphosphonium salt followed by Wittig reaction. II. Synthesis of cyclopropyl oxylipins by a cation mediated carbocyclization

Studies toward the total synthesis of phorboxazole A

The synthesis of trisporic acids

Chiral synthesis of monic acid C

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