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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

Synthesis of metabolites from the ascomycetes : I. The synthesis and absolute configuration of leptosphaerin : II. Approaches to the synthesis of byssochlamic acid

Creator:: Pallenberg, Alexander J.
Abstract:: Part I. The total synthesis of (+)-leptosphaerin (2), a metabolite of the marine Ascomycete Leptosphaeria Oraemaris (Linder) was achieved, unambiguously establishing both the relative and absolute stereochemistry of this natural product. This synthesis also resolved the long-standing question of which of the isomeric structures 1 or 2 correctly represents the...
Resource Type:: Dissertation
Full Text:: group. Schmidt also described the manipulations necessary to obtain 48 and to remove the phenylthio and

Studies toward the total synthesis of phorboxazole A

Creator:: Kuntiyong, Punlop
Abstract:: Studies toward the total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, were conducted and resulted in a route to an advanced intermediate, C4-C32, for this purpose. A key feature of our approach is the stereoselective synthesis of two cis-2,6-disubstituted tetrahydropyrans present in the macrolide portion of...
Resource Type:: Dissertation
Full Text:: , M. D.; Doubek, D. L.; Boyd, M. R.; Schmidt, J. M.; Chapuis, J-C.; Hamel, E.; Bai, R.; Hooper, J. N

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

Creator:: Ruppert, John Fredrick
Resource Type:: Dissertation
Full Text:: stereohomogeneity of 97 was threefold. The interconversion of the E and Z isomers of 94 is faster than ylide

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:: (+) 2R,3R,2-METHYL-2,3-ISOPROPYLID- 12 E-NE DIOXYPENTANAL III. AN APPROACH TO SEGMENT B FROM

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

The synthesis of macrolactones from [omega]-hydroxyacyl xanthates

Creator:: Akella, Annapoorna
Resource Type:: Masters Thesis
Full Text:: TISCMe3 Hg(OCOCF3)2 (CH 1 e 3 2)n SCM (CH2)n SCMe3 &mu., 2+ H 25 OH 24 8 9 The Mukaiyama

Synthetic transformations of shikimic acid

Creator:: White, Edward D., III
Abstract:: Four strategies which involve synthetic elaboration of the shikimate nucleus are discussed. Methyl shikimate was differentially protected as the 3,4-0-cyclopentylidene ketal and as the 5- 0- tert- butyldiphenylsilyl ether. The methyl ester was then reduced with diisobutylaluminum hydride and the resulting allylic alcohol was oxidized to aldehyde 47 with pyridinium...
Resource Type:: Masters Thesis
Full Text:: first discovered in studies on auxotrophic mutants of E. coli and Aerobacter aerogenes.1 Figure 1

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:: thickness 0.2 mm, manufactured by E. Merck). Unless otherwise indicated, products were visualized by

ScholarsArchive@OSU

Absolute stereochemistry and total synthesis of botryococcene

Chiral synthesis of monic acid C

Synthesis of metabolites from the ascomycetes : I. The synthesis and absolute configuration of leptosphaerin : II. Approaches to the synthesis of byssochlamic acid

Studies toward the total synthesis of phorboxazole A

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

Approaches to the synthesis of methymycin

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

The synthesis of macrolactones from [omega]-hydroxyacyl xanthates

Synthetic transformations of shikimic acid

Approaches toward synthesis of the mycosporins

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