Index Catalog // ScholarsArchive@OSU

Total synthesis of (+)-bourgeanic acid and conformational analysis of its dilactone

Creator:: Johnson, Alan T. (Alan Thomas), 1957-
Resource Type:: Dissertation
Full Text:: analysis of its dilactone AN ABSTRACT OF THE THESIS OF Alan T. Johnson for the degree of Doctor of

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:: aqueous hydrogen fluoride produced kendomycin 1. OMe TBSO O I O HO O I t-BuLi, Et2O, THF; 9-BBN

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:: cyclosporine A 1.4 References 1. Fehr, T.; Oberer, L.; Ouesniaux Ryffel, V.; Sanglier, J.-J.; Schuler, W

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:: DIHYDROPYRAN a cCt:r 58 i + b 53 54 l J i C OtOBORN 55 1 d t 010 59 60 Reagents: a) Br2; b) 1

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:: ethyldiazoacetate to give 4-carboxyethyl-l-methoxy-5-methyltricyclo[5.1.0.03'5]octane 26. Acid catalyzed

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:: % ee 79% 1. L.CrCI (4 mol%) + 0 t-BuOMe, -35 to 5 °C Ph) 2. TfOH 28 0 Ph 32 L = 25: yield 85% L

Total synthesis of (-)-7-epicylindrospermopsin

Creator:: Hansen, Joshua D.
Abstract:: The first asymmetric synthesis of (-)-7-epicylindrospermopsin via intramolecular nitrone cycloaddition is described. The synthesis utilized a convergent approach to prepare the cycloaddition precursor 176, which was assembled by condensation of hydroxylamine 175 with aldehyde 145. Hydroxylamine 175 was synthesized from ethylene glycol (166) in seven steps. Aldehyde 145 was completed...
Resource Type:: Dissertation
Full Text:: inhibition exerted by cylindrospermopsin is still unclear. 7 Either l"glutamylcysteine synthetase or

Approaches toward the asymmetric synthesis of pillaromycin A

Creator:: Nolen, Ernest G.
Resource Type:: Dissertation
Full Text:: )-7-acryloxy-8-acetoxy-2-t-butyldimethyl- siloxy-3,5-nonadiene (59). Three Diels-Alder products were

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:: phenoxymethyl side chain to yield 20, hydrolysis of the t-butyl ester set the stage for ring closure. This was

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

ScholarsArchive@OSU

Total synthesis of (+)-bourgeanic acid and conformational analysis of its dilactone

Studies towards the total synthesis of (-)-kendomycin

Studies toward the total synthesis of sanglifehrin A

Chiral synthesis of monic acid C

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

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

Total synthesis of (-)-7-epicylindrospermopsin

Approaches toward the asymmetric synthesis of pillaromycin A

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

Total synthesis of indole alkaloids: pt. 1. Asymmetric synthesis of (-)-ibogamine. pt. 2. An approach toward the synthesis of koumine

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