Index Catalog // ScholarsArchive@OSU

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:: rapamycin AN ABSTRACT OF THE DISSERTATION OF Scott C. Jeffrey for the degree of Doctor of Philosophy in

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

Creator:: Ruppert, John Fredrick
Resource Type:: Dissertation
Full Text:: the synthesis of mycosporin (P 310) AN ABSTRACT OF THE THESIS OF John Fredrick Ruppert for the

Studies toward the total synthesis of (+)-providencin

Creator:: Jana, Somnath
Abstract:: Studies toward the total synthesis of (+)-providencin (1), a highly oxygenated cembranoid dipterpene with a unique bicyclo[12.2.0]hexadecane skeleton and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediates 320 and 332 which contain all of the carbon atoms of 1. In a first generation approach...
Resource Type:: Dissertation
Full Text:: , Professor Rich G. Carter, Professor Paul R. Blakemore, Professor Kevin P. Gable, Professor Janet Tate and

Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

Creator:: Li, Yang
Abstract:: Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient...
Resource Type:: Dissertation
Full Text:: P. Gable, Dr. Jamie J. Kruzic and Dr. Kerry L. McPhail for their support and time. I deeply

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:: characterization of the new salen ligand and its complexes with various transition and p- block metals. Chapter 3

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:: and A.I. Scott (9) con- structs masked polyketide systems with the P-diketone units protected in the

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
Full Text:: of 76 and 66 with phthalimidoacetyl chloride respectively. Attempted p-lactam formation by

Synthesis of furanoeremophilane sesquiterpenoids

Creator:: Shanmugham, Meenakshi Sundaram
Abstract:: Two approaches to the tricyclic core of the furanoeremophilane sesquiterpenoids are described. The first approach entails a projected Diels-Alder/retro Diels-Alder reaction of an acetylenic oxazole 64. Construction of the pivotal aldehyde 67 commenced from ketone 68. The acetyenic moiety was then introduced via a Felkin-Ahn addition of lithiopropyne to aldehyde...
Resource Type:: Dissertation
Full Text:: , Nick Drapela, Uwe Grether, Roger Hanselmann, Josh Hansen, Bryan Hauser, David IhIe, Scott Kemp, Linda

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:: Hansen, Carla Hassler, Bryan Hauser, Eric Hong, Peter Hrnciar, Scott Kemp, Linda Keown, Jungchul Kim

Synthetic studies of nonadrides

Creator:: Drapela, Nicholas Ernest
Abstract:: An asymmetric approach to the synthesis of byssochlamic acid (1) is described. Regioisomeric enzymatic differentiation is described in the selective hydrolysis of dimethyl ester 30 by porcine liver esterase. Chiral dimethyl ester 42 was prepared by desymmetrization of cyclopentene 34 using porcine liver esterase. A key intramolecular [2+2]cycloaddition-cycloreversion photometathesis of...
Resource Type:: Dissertation
Full Text:: by an X-ray crystal structure of its bis-p-bromophenylhydrazide 10.14 Finally, the absolute

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:: 23 IV Experimental 54 V Bibliography 96 LIST OF TABLES Table I Oxidative Coupling of p-Cresol

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:: closed to form the furan 29 in the presence of p-toluenesulfonic acid in refluxing benzene. Cyclization

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

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

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:: Deerberg, Duncan J. Wardrop, Carla Hassler, Sung-kee Kim, Christine S. Nylund, Scott J. Kemp, Roger

Synthetic studies on marine natural products : Part 1. Synthesis of the sesquiterpenoid dihydropallescensin D via manganese(III)- mediated carbocyclization. Part 2. Approaches toward the synthesis of prianosin and discorhabdin alkaloids

Creator:: Yager, Kraig M.
Resource Type:: Dissertation
Full Text:: , particularly John Amedio, Alan Johnson, Motoji Kawasaki, Steve Toske, Scott Jeffrey, Mark Jensen, Frank

Part I : synthesis of azetidin-2-ones from pyrazolidin-3-ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506

Creator:: Toske, Steven Gerald
Resource Type:: Dissertation
Full Text:: overall yield of 1.3%. Treatment of a,p-unsaturated-S-lactone 211, prepared from 208 in three steps, with

Absolute stereochemistry and total synthesis of botryococcene

Creator:: Reddy, Guvvala Nagabhushana
Abstract:: Studies were carried out to determine the absolute stereochemistry of botryococcene (1). The natural product was degraded to two sets of 'y- and 8- valerolactones. All enantiomeric variations of these lactones were synthesized in optically pure form starting from (S)- and (R)-methyloxiranes. 1H NMR correlation of natural and synthetic materials...
Resource Type:: Dissertation
Full Text:: attached to a tetrasubstituted carbon atom. Botryococcene could also be partially reduced with P-2 nickel

Synthetic studies on necic acids of pyrrolizidine alkaloids

Creator:: Lee, Nadine Chauyi
Resource Type:: Dissertation
Full Text:: study at OSU more fun and enjoyable. Postdoctors: Fraser F. Fleming, Warren J. Porter, Michael P

Synthetic studies on the macrolide antibiotic rutamycin B

Creator:: Wang, Shan
Resource Type:: Dissertation
Full Text:: , Nick Drape la, Neal Green, Carla Hassler, Mark Holoboski, Randy Jackson, Scott Jeffrey, Scott Kemp

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

Creator:: Skeean, Richard William
Resource Type:: Dissertation
Full Text:: Lewis acid (zinc chloride), or a protic acid (p-tol- uenesulfonic), or even upon long standing with

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:: - dimethylcyclohexane,p -TsOH; b) (Me0)2P(0)CH2CO2t-Bu, NaH, LiBr 45 The esters 88 and 89 were then hydroxylated

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:: members of the White group, particularly Frank Stappenbeck, No-soo Kim, Tae-seong Kim, Scott Jeffery

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:: direction that could be adapted to this strategy. First, the p-methoxybenzyl group was removed from 1 2

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