Index Catalog // ScholarsArchive@OSU

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:: -borneol, PhNMe2; c) DBU; d) m-chloroper- benzoic acid ''OBORN 61 BORN 26 : B OBORN 62 27

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:: , L. C.; Gois, P. M. P.; Lourenco, N. M. T.; Kurteva, V. B.; Afonso, C. A. M. Chem. Commun. 2006

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

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:: AN ABSTRACT OF THE DISSERTATION OF Christopher M. Lincoln for

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:: homolysis of nitromethane.51 Hirao and co-workers have shown that M n (OA c) 3 effectively catalyzes

Alkylation studies on Hagemann's ester: an approach to the synthesis of the trisporic acids

Creator:: Sung, Wing Lam
Abstract:: Sequential alkylation of Hagemann's ester with methyl and methallyl halides has been studied. Treatment of Hagemann's ester with methyl iodide and sodium ethoxide gave a mixture of 21 and 25 in a ratio of 4:1. Alkylation of 21 with methallyl chloride and potassium t-butoxide afforded a mixture of 37 and...
Resource Type:: Masters Thesis
Full Text:: ); mass spectrum m/e 210 (M+). Anal Calcd for 24 C12H1803:C, 68. 55; H, 8.65. Found: C, 68. 36; H, 8.73

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:: m/e (relative intensity) 293 (M+, 94.9), 262 (12.9), 142 (100); Anal. Calcd for C16H23N04: C, 65.51

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:: the hope of introducing the keto group required at C-7, the mesylate 78 was epoxidized with m

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:: two main subunits via C-C bond formation at C9-C1 0. In addition, through modifications to the C9-C1

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:: sanglifehrin A, C60H89N5O12 (m/z 1078, [M+Li]+) for B, C61H93N5O13 (m/z 1110, [M+Li]+) for C, and

ScholarsArchive@OSU

Chiral synthesis of monic acid C

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

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

Asymmetric synthesis of cyclopropanes via a "zipper reaction"

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

Alkylation studies on Hagemann's ester: an approach to the synthesis of the trisporic acids

Approaches to the total synthesis of verrucarol

Approaches to the synthesis of methymycin

Synthesis of epothilones and epothilone analogues

Studies toward the total synthesis of sanglifehrin A

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