Index Catalog // ScholarsArchive@OSU

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:: kendomycin. Several methods for isomerizing Z olefin 30 to an E olefin were explored, but the only

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

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:: desired E-butenoate as the major product. Selec- tive reduction of the methyl ester of these diesters

Approaches toward the asymmetric synthesis of pillaromycin A

Creator:: Nolen, Ernest G.
Resource Type:: Dissertation
Full Text:: ; R 2 =H, aklavinone R1=H; R 2 =OH, E-rhodomycinone R1=0H; R 2 =H, E-pyrromycinone H 0- SUGAR

Synthetic studies on alkaloids : part I, an approach toward the synthesis of (̳+)-koumine : part II, an approach toward the synthesis of (̳+)-morphine

Creator:: Stappenbeck, Frank
Resource Type:: Dissertation
Full Text:: approach entails a projected intramolecular Michael addition of the butenolide 96. The second route

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

Creator:: Skeean, Richard William
Resource Type:: Dissertation
Full Text:: prepared in tetrahydrofuran by suc- 2R ,-/-"NN OH E+ .`CO2R Figure 9 cessive treatment with sodium

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:: , and Michael Alan and my parents ACKNOWLEDGEMENTS I wish to express my sincere appreciation to

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:: first discovered in studies on auxotrophic mutants of E. coli and Aerobacter aerogenes.1 Figure 1

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
Full Text:: predominance of intermediate 3 was shown after a spontaneous internal Michael addition led to Pummerer's

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:: , Paul R. Blakemore, Cindy Browder, Rich G. Carter, Bobby Chow, Jorg Deerberg, Nicholas E. Drapela, Uwe

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:: , Lonnie Robarge, Volker schulze, Keith Schwartz, Helmars Smits, Kurt Sunderman, Michael Thutewohl

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
Full Text:: and is thus suitably positioned to catalyze the postulated Michael addition CHO C it RSH 14 CHO

Synthetic studies n bioactive natural products. Part I, An approach towards the nootrophic agent huperzine A. Part II, Synthesis of the tricarbonyl subunit of rapamycin

Creator:: Jeffrey, Scott C.
Resource Type:: Dissertation
Full Text:: , Carman Somoza, and Joey Carson Graduate Committee Peter Freeman, Michael Schimerlik, Jim Krueger

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
Full Text:: to be the result of initial Michael attack by thiol on the double bond of 110. Carboxyl activation

Synthesis of two subunits of avermectin B1a

Creator:: Dantanarayana, Anura Pathmasiri
Abstract:: Avermectins are a group of potent anthelmintic agents produced by Streptomyces avermitilis. They are active at extremely low dosages and are now in commercial use. In this study, the synthesis of two segments of avermectin B[subscript 1a] are described. The synthesis of the hexahydrobenzofuran subunit (segment A) began with the...
Resource Type:: Dissertation
Full Text:: conditions, was transformed to the bicyclic ketone 55 via an intramolecular Michael addition. Selective

Synthetic studies on natural products : Part I. The total synthesis of ±-euonyminol and ±-3,4-dideoxymaytol : Part II. The absolute configuration and enantioselective synthesis of curacin A

Creator:: Kim, Tae-Seong
Resource Type:: Dissertation
Full Text:: . The Total if _ -E in min 4-13- m. 1 P rt II. Th- A of to Configuration and Enantioselective

An approach toward the synthesis of euonyminol and cathedulin K- 19

Creator:: Shin, Hyunik
Abstract:: A synthetic approach toward the two major fragments of cathedulin K-19, euonyminol (4) and dimethyl cathate (69), was investigated. Synthesis of dimethyl cathate was accomplished in 3 steps starting from 73. Efforts directed towards the synthesis of euonyminol, a highly oxygenated dihydroagarofuran sesquiterpene, was advanced to a stage in which...
Resource Type:: Dissertation
Full Text:: weight group includes E-2 (19) and E-8 (20),19 both based on the core structure 10 . The medium

Synthesis of marine natural products. part I, Cryptophycins-1, -3, -4, -24, and -29, part II, Polycavernoside A

Creator:: Robarge, Lonnie A.
Resource Type:: Dissertation
Full Text:: developed in which (5S, 6R)-5-hydroxy-6-methyl-8-phenylocta-2(E), 7(E)-dienoic acid (A) was coupled with

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

Chiral synthesis of monic acid C

Approaches toward the asymmetric synthesis of pillaromycin A

Synthetic studies on alkaloids : part I, an approach toward the synthesis of (̳+)-koumine : part II, an approach toward the synthesis of (̳+)-morphine

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

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

Synthetic transformations of shikimic acid

Phenolic oxidative coupling : an approach to the synthesis of pretazettine

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

Studies toward the total synthesis of phorboxazole A

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

Synthetic studies n bioactive natural products. Part I, An approach towards the nootrophic agent huperzine A. Part II, Synthesis of the tricarbonyl subunit of rapamycin

Approaches to the synthesis of polyketides. Vermiculine

Synthesis of two subunits of avermectin B1a

Synthetic studies on natural products : Part I. The total synthesis of ±-euonyminol and ±-3,4-dideoxymaytol : Part II. The absolute configuration and enantioselective synthesis of curacin A

An approach toward the synthesis of euonyminol and cathedulin K- 19

Synthesis of marine natural products. part I, Cryptophycins-1, -3, -4, -24, and -29, part II, Polycavernoside A

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