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Approaches to the synthesis of trichothecenes

Creator:: Kim, No-soo
Resource Type:: Dissertation
Full Text:: Abstract of the Thesis of No-Soo Kim for the degree of Doctor of Philosophy in Chemistry presented on

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:: for C 9 H 15 NO 4 201.100). 36 3-Acetoxy-5-(1,2-0-isopropylidene dihydroxyethyl)- 3-pyrrolin-2

Approaches toward synthesis of the mycosporins

Creator:: Cammack, Janice H.
Abstract:: The mycosporins, formerly called P310's are secondary metabolites of fungi closely associated with fungal reproductive processes that require light. The structurally related iminomycosporins are found in marine plants and animals and may also have functions related to light. In this study, approaches toward the asymmetric synthesis of the mycosporins are...
Resource Type:: Dissertation
Full Text:: . Protection of (1R,2S13R15R)-1,2-0-cyclopentylidene-1,2,315- tetrahydroxy-5-hydroxymethylcyclohexane (39) and

The total synthesis of (-)- acorenone B ; Approaches to the synthesis of mycosporin (P 310)

Creator:: Ruppert, John Fredrick
Resource Type:: Dissertation
Full Text:: and 50 into Spiro[ 4. 51 decanones and spiro[5. 5]undecanones respectively, as well as into

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:: photolysis of 77 or 78 yielded only Norrish type II cleavage and no cyclization product. Biogenetically

Synthetic studies of nonadrides

Creator:: Drapela, Nicholas Ernest
Abstract:: An asymmetric approach to the synthesis of byssochlamic acid (1) is described. Regioisomeric enzymatic differentiation is described in the selective hydrolysis of dimethyl ester 30 by porcine liver esterase. Chiral dimethyl ester 42 was prepared by desymmetrization of cyclopentene 34 using porcine liver esterase. A key intramolecular [2+2]cycloaddition-cycloreversion photometathesis of...
Resource Type:: Dissertation
Full Text:: racemic diester was converted to monoacid. No other products were isolated except a small amount (<5%) of

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:: oxazabicyclo[2.2.1 ]heptane derivative 177 accompanied by two unidentified stereoisomers in a ratio of 10:5

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:: Diels-Alder reaction, exceptions 3 are common. For example,with methacrolein 5 and cyclopentadiene

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:: its iodide. Methyl (2R)-3-hydroxy-2-methylpropionate was transformed into methoxy- methyl ( 5S)- 2, 5

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:: hydrolysis, (±)-(7E, 9E)-trisporic acid B (3). Treatment of 3 with diazomethane afforded a 5% yield of

ScholarsArchive@OSU

Approaches to the synthesis of trichothecenes

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

Approaches toward synthesis of the mycosporins

The total synthesis of (-)- acorenone B ; Approaches to the synthesis of mycosporin (P 310)

Approaches to the synthesis of penicillin

Synthetic studies of nonadrides

Total synthesis of (-)-7-epicylindrospermopsin

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

Absolute stereochemistry and total synthesis of botryococcene

The synthesis of trisporic acids

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