Index Catalog // ScholarsArchive@OSU

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

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

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:: -[(methoxymethypoxy]-3-E-hexenoate (126 and 127), and an organocopper coupling reaction. Methyl (2S)-3-hydroxy-2

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 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:: of the primary alcohol of 102, followed by introduction of the E-ethylidene group, furnished 31

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:: References 1. Livesey, G.; Brown, J. C. J. Nutr. 1995, 125, 3020. 2. Raymer, G. S.; Hartman, D. E.; Rowe, W

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
Full Text:: - ethoxy-l-viny1)-furan (42) 49 2- (2 - Hydroxy- e thyl) - 5 - (2 - hydr oxy- propyl) furan (45) 49 2- (2

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:: (3 H, s), 1.9 (3 H, s), 1.7 (3 H, d, J = 6 Hz); MS m/e 180.116 (M+, calc for C 11 H 16 0 2 180.115

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:: ) Phorboxazole A.. 2 151 153 235 LIST OF TABLES Table Page 2.1 E/Z Isomerization

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:: a functional group (e. g. methoxy4) at C-6 of the penicillin nucleus. This structural modification

ScholarsArchive@OSU

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 towards the total synthesis of (-)-kendomycin

Absolute stereochemistry and total synthesis of botryococcene

Chiral synthesis of monic acid C

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

Cis-2,5-diaminobicyclo[2.2.2]octane : a novel C₂-symmetric scaffold for asymmetric catalysis

The synthesis of nonactic acid

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

Total synthesis of phorboxazole A

Approaches to the synthesis of penicillin

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