Index Catalog // ScholarsArchive@OSU

Total synthesis of phorboxazole A

Creator:: Lee, Tae Hee
Abstract:: The total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, is described. Both a palladium(II)-mediated and a palladium(II)-catalyzed intramolecular alkoxycarbonylation were used as key steps for the preparation of the two cis-2,6-disubstituted tetrahydropyran rings (C22-C26 and C11-C15) of phorboxazole A. The synthesis used a convergent approach involving...
Resource Type:: Dissertation
Full Text:: Rights Reserved TOTAL SYNTHESIS OF PHORBOXAZOLE A by Tae Hee Lee

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:: of Polyketides. V ermiculine. by Curtis Lee Kirkemo A THESIS submitted to Oregon State

Synthetic studies on necic acids of pyrrolizidine alkaloids

Creator:: Lee, Nadine Chauyi
Resource Type:: Dissertation
Full Text:: on Necic Acids of Pyrrolizidine Alkaloids by Nadine Chauyi Lee A DISSERTATION submitted to

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:: , -3, -4, -24, and -29, part II, Polycavernoside A. AN ABSTRACT OF THE DISSERTATION OF Lonnie A

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:: [2.2.2]octane: A Novel C2-Symmetric Scaffold for Asymmetric Catalysis Abstract approved: James D

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:: :_____________________________________________________ James D. White Studies towards the total synthesis of (−)-kendomycin (1), a bacterial

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:: TOTAL SYNTHESIS OF PHORBOXAZOLE A. Abstract approved: James D. White Studies toward the total

Asymmetric synthesis of cyclopropanes via a "zipper reaction"

Creator:: Lincoln, Christopher M.
Abstract:: The rearrangement of a homoallyl cation to a cyclopropylcarbinyl cation is thought to play a role in the biogenesis of a variety of cyclopropane-containing natural products,¹ a hypothesis which has previously led to the design of successful biomimetic syntheses of several natural products.² The strategy underlying this approach to cyclopropane...
Resource Type:: Dissertation
Full Text:: Synthesis of Cyclopropanes via a "Zipper Reaction" Abstract approved: James D. White The rearrangement of

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:: Title: Studies Toward the Total Synthesis of Sanglifehrin A. Abstract approved

Synthesis of a model of the spiroketal portion of avermectin B

Creator:: Warrier, Ulhas S.
Abstract:: Avermectin Bia is a member of a class of medicinally important natural products known for its potent antiparasitic activity and interesting structural features. In this thesis, synthesis of a model for the spiroketal portion of the avermectins is presented. Oxidation of (S)-2-methylbutanol, followed by a stereoselective chromium mediated reaction with...
Resource Type:: Masters Thesis
Full Text:: Synthesis of a model of the spiroketal portion of

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:: . Stereoselective synthesis of E,Z-1,3-Dienes by tandem nucleophilic addition to a dienylphosphonium salt followed

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:: synthesis of curacin A AN ABSTRACT OF THE DISSERTATION OF Tae-Seong Kim for the degree of Doctor of

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:: , Wolfgang Wenger, Uwe Grether, Laura Quaranta, Nicholas E. Drapela, Nadine Lee, Peter Hrnciar, Lonnie A

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:: approach towards the nootrophic agent huperzine A. Part II, Synthesis of the tricarbonyl subunit of

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:: -ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506 AN ABSTRACT OF THE THESIS OF

Synthetic studies on alkaloids : part I; asymmetric synthesis of (±) codeine. Formal synthesis of (±) morphine : part II; a unified asymetric approach toward synthesis of polyhydroxylated pyrrolizidine alkaloids, australine and alexine

Creator:: Hrnciar, Peter
Resource Type:: Dissertation
Full Text:: Alkaloids. Part I: Asymmetric Synthesis of (+)- Codeine. Formal Synthesis of (+)-Morphine. Part II: A

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:: Cathedulin K-19. Abstract approved by: A synthetic approach toward the two major fragments of cathedulin K

Studies towards the total synthesis of (-)-gymnodimine

Creator:: Wang, Guoqiang
Abstract:: Studies towards the total synthesis of (-)-gymnodimine (1), a marine neurotoxin with a unique molecular architecture and pronounced biological activity, are described. These studies resulted in a convergent approach to the advanced intermediate 315, containing the C3-C32 section of 1. Two synthetic routes were developed to construct the tetrahydrofuran subunit...
Resource Type:: Dissertation
Full Text:: ()-gymnodimine (1), a marine neurotoxin with a unique molecular architecture and pronounced biological activity

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:: the total synthesis of (+)-providencin (1), a highly oxygenated cembranoid dipterpene with a unique

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:: furanoeremophilane sesquiterpenoids are described. The first approach entails a projected Diels- Alder/retro Diels

Approaches to the total synthesis of verrucarol

Creator:: Hill, David E. (David Edwin) 1954-
Abstract:: Verrucarol is the sesquiterpene portion of a number of macrocyclic di- and triesters of potential medicinal importance. In this study, a novel approach to the synthesis of this fungal metabolite is presented. An A-B-C route was investigated in which C-3 and C-4 of the C-ring were emplaced using a [2+2]...
Resource Type:: Dissertation
Full Text:: privacy (Pr. James D. White Verrucarol is the sesquiterpene portion of a number of macrocyclic di- and

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:: Epothilones and Epothilone Analocjues. Abstract approved: A convergent synthesis of epothilone B that

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
Full Text:: , followed by a cuprate mediated methylation, gave a 1:1 mixture of (2S) -3- methyl -1,2- butanediol and

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:: fourteen steps from benzoquinone and in 10% overall yield is a powerful illustration of the value of the

Synthetic approaches to the tricarbonyl subunit of rapamycin

Creator:: LaMunyon, James B.
Abstract:: Rapamycin (5) was isolated in 1975 from the soil bacteria Streptomyces hygroscopicus and its structure was determined from spectroscopic techniques and an x-ray crystallographic analysis. Although it was initially found to exhibit antibiotic activity, it was subsequently shown to possess potent immunosuppressive activity as well. Three approaches to the synthesis...
Resource Type:: Masters Thesis
Full Text:: the synthesis of 127 envisioned a rearrangement of the a-acyloxy amide 135 to 136 followed by

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:: NAcy1-2-thionothiazolidines Abstract approved: Redacted for privacy DT. James D. White Part I A total

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:: compounds were compared as oxidants for the conversion of 32 to 33. In an approach directed at a synthesis

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:: cycloaddition to yield a 4.3:1 mixture of trans-3a-hydroxymethy1-18,6a-dimethyl-la-methoxycarbonyl- cyclohex-4

Approaches to the synthesis of trichothecane sesquiterpenes

Creator:: Thomas, James Anthony
Resource Type:: Dissertation
Full Text:: with the ultimate goal of an efficient synthesis of a member of the trichothecane class of

Structural and synthetic studies of higher terpenoids : Part I. The absolute configuration of (-)-botryococcene : Part II. Total synthesis of (±)-2-desoxystemodinone

Creator:: Somers, Todd Charles
Resource Type:: Dissertation
Full Text:: centers in 1 as 3S,7S,10S113R,16S120S. Application of a similar degradation protocol to braunicene (10

Approaches to the synthesis of trichothecenes

Creator:: Kim, No-soo
Resource Type:: Dissertation
Full Text:: this study, a novel approach to the synthesis of these sesquiterpenoids is presented. A B-A-C route

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:: dihydropallescensin D (82), a sesquiterpenoid related to the sponge metabolite pallescensin D (16), is described

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
Full Text:: . Redacted for privacy Abstract approved: James D. White A formal total synthesis of the macrolactone

Synthetic studies on the macrolide antibiotic rutamycin B

Creator:: Wang, Shan
Resource Type:: Dissertation
Full Text:: approach to 53 was based on addition of a higher order cuprate derived from iodide 60 to epoxide 59

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