Index Catalog // ScholarsArchive@OSU

Alkylation studies on Hagemann's ester: an approach to the synthesis of the trisporic acids

Creator:: Sung, Wing Lam
Abstract:: Sequential alkylation of Hagemann's ester with methyl and methallyl halides has been studied. Treatment of Hagemann's ester with methyl iodide and sodium ethoxide gave a mixture of 21 and 25 in a ratio of 4:1. Alkylation of 21 with methallyl chloride and potassium t-butoxide afforded a mixture of 37 and...
Resource Type:: Masters Thesis

The synthesis of nonactic acid

Creator:: Arco, Manuel Jose
Abstract:: Alkylation of propylene oxide with 2-lithiofuran gave alcohol I, which was smoothly converted to acetylfuran II. hydrogenation of II over rhodium on charcoal followed by Jones' oxidation afforded ketone III. Further transformation into IV was accomplished via a Wittig reaction followed by saponification with methanolic sodium hydroxide. Hydroboration of the...
Resource Type:: Dissertation

Approaches to the synthesis of polyketides. Vermiculine

Creator:: Kirkemo, Curtis Lee
Abstract:: An approach to the generation of polyketides was investigated, which involved ozonolysis of 6, 7 cyclopenteno -1> 4, 5, 8 -tetrahydromethoxy- 3-methylnaphthalene (26), to produce what is believed to be polyketide 27. Compound 26 was formed by the following sequence: Die ls -Alder addition of 1, 2 -dim.ethylenecyclopentane and 2...
Resource Type:: Dissertation

Approaches to the synthesis of penicillin

Creator:: Furuta, Takuya
Abstract:: Several approaches to the synthesis of penicillin from 2-iminothioazolidine 50, from 2-thiothiazolidine 66 and by photocyclization of 77 and 78 were investigated. 2-Iminothiazolidine 50 was prepared from dibromoester 45 by the action of benzylamine followed by treatment of aziridine 46 with potassium or ammonium thiocyanate. Attempted introduction of a two-carbon...
Resource Type:: Dissertation

The total synthesis of (-)- acorenone B ; Approaches to the synthesis of mycosporin (P 310)

Creator:: Ruppert, John Fredrick
Resource Type:: Dissertation

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

Approaches to the synthesis of trichothecane sesquiterpenes

Creator:: Thomas, James Anthony
Resource Type:: Dissertation

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

Creator:: Skeean, Richard William
Resource Type:: Dissertation

Approaches to the synthesis of methymycin

Creator:: Raghavan, Palaykotai Rajagopalan
Abstract:: Several approaches to the synthesis of methymycin were investigated. Segment A (39), containing functionality corresponding to C-9, 10, and 11 of methynolide was made in six steps from propionaldehyde in an overall yield of 37%. Oxidation of 34 with silver nitrate gave 35 which, upon hydroxylation with hydrogen peroxide, gave...
Resource Type:: Dissertation

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

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

Part I. The total synthesis of (±)-cinnamodial and related drimane sesquiterpenes; Part II. Photochemical activation of the carboxyl group via N-Acyl-2-thionothiazolidines

Creator:: Burton, Lester Percy Joseph
Resource Type:: Dissertation

Condensation of crotonic and tiglic acids with aldehydes and ketones

Creator:: Johnson, Paul Robert
Resource Type:: Masters Thesis

Phenolic oxidative coupling : an approach to the synthesis of pretazettine

Creator:: Chong, Wesley Kwan Mung
Abstract:: Various hypervalent iodine compounds were evaluated as reagents for intramolecular phenolic oxidative coupling. It was found that phenyliodine(III) bis(trifluoroacetate) was effective for the coupling of the monophenolic substrate 13a to 14a under neutral conditions. Vanadium oxytrifluoride and hypervalent iodine compounds were compared as oxidants for the conversion of 32 to...
Resource Type:: Dissertation

Chiral synthesis of alcohols via asymmetric epoxidation

Creator:: Engebrecht, Jeffrey Ronald
Abstract:: Enantioselective epoxidation of crotyl alcohol, followed by a cuprate mediated methylation, gave a 1:1 mixture of (2S) -3- methyl -1,2- butanediol and (2R,3S)-2-methy1-1,3- butanediol. The latter was separated as its 2,4,6-trimethylbenzenesulfonate derivative and converted via the iodide to the corresponding phosphonium salt. The separated butanediol derivatives were independently transformed to...
Resource Type:: Masters Thesis

Studies on the synthesis of the "northern" and "southern" segments of boromycin and aplasmomycin

Creator:: Kang, Myung Chol
Abstract:: The stereocontrolled synthesis of the southern lactone 17 of boromycin and of the northern segments of both boromycin and aplasmomycin are described. The syntheses begin with enantioselective epoxidation of 3-buten-2-ol (42) to provide the optically active 2(S),3(R) epoxy alcohol 43. The absolute configuration was confirmed by preparing 43 from (-)-2,3-dihydroxybutyric...
Resource Type:: Dissertation

Approaches toward the asymmetric synthesis of pillaromycin A

Creator:: Nolen, Ernest G.
Resource Type:: Dissertation

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

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

Approaches to the synthesis of the macrolactone pyrrolizidine alkaloids (-)-integerrimine and (+)-usaramine

Creator:: Jayasinghe, Lalith Ratnasiri
Abstract:: A formal total synthesis of the macrolactone pyrolizidine alkaloid (-)-integerrimine (2), from R-(+)-citronellal (93) is described. Aldehyde 93 was converted to exo methylene derivative 94 which was reduced to allylic alcohol 95. The epoxides 96 and 98, obtained in a ratio of 3:1 respectively by Sharp less epoxidation of 95...
Resource Type:: Dissertation

ScholarsArchive@OSU

Alkylation studies on Hagemann's ester: an approach to the synthesis of the trisporic acids

The synthesis of nonactic acid

Approaches to the synthesis of polyketides. Vermiculine

Approaches to the synthesis of penicillin

The total synthesis of (-)- acorenone B ; Approaches to the synthesis of mycosporin (P 310)

The synthesis of trisporic acids

Approaches to the synthesis of trichothecane sesquiterpenes

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

Approaches to the synthesis of methymycin

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

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

Part I. The total synthesis of (±)-cinnamodial and related drimane sesquiterpenes; Part II. Photochemical activation of the carboxyl group via N-Acyl-2-thionothiazolidines

Condensation of crotonic and tiglic acids with aldehydes and ketones

Phenolic oxidative coupling : an approach to the synthesis of pretazettine

Chiral synthesis of alcohols via asymmetric epoxidation

Studies on the synthesis of the "northern" and "southern" segments of boromycin and aplasmomycin

Approaches toward the asymmetric synthesis of pillaromycin A

Chiral synthesis of monic acid C

Synthetic transformations of shikimic acid

Approaches to the synthesis of the macrolactone pyrrolizidine alkaloids (-)-integerrimine and (+)-usaramine

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