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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

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:: over rhodium on charcoal followed by Jones' oxidation afforded ketone III. Further transformation into

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:: ABSTRACT OF THE THESIS OF David E. Hill for the degree of Doctor of_Philosophy in Chemistry presented on

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

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
Full Text:: followed by oxidation by Jones' reagent, gave 53. Treatment of 53 with methyl magnesium iodide in the

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:: enzyme present in vivo, converts the (R) e n anti o me r of 6 to the active (S)-enantiomer.4 / NH 0 0

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:: appreciated. I thank Professor Stanley E. Wilson for his always optimistic outlook, and also Dr. Carl N

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:: . Structure Elucidation C. Synthesis of the Putative Leptosphaerin D. Experimental E. Bibliography 1 4 9

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

The synthesis of nonactic acid

Approaches to the total synthesis of verrucarol

Absolute stereochemistry and total synthesis of botryococcene

Approaches to the synthesis of methymycin

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 trisporic acids

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

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