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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:: derivative 152 and elaboration of the side chain to provide an efficient route to 164. Initial attempts at

Synthesis of two subunits of avermectin B1a

Creator:: Dantanarayana, Anura Pathmasiri
Abstract:: Avermectins are a group of potent anthelmintic agents produced by Streptomyces avermitilis. They are active at extremely low dosages and are now in commercial use. In this study, the synthesis of two segments of avermectin B[subscript 1a] are described. The synthesis of the hexahydrobenzofuran subunit (segment A) began with the...
Resource Type:: Dissertation
Full Text:: phosphonium salt. An attempted Wittig reaction of the ylid derived from 152 with 120 failed to give the

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:: 152. 119 2.4 ORTEP representation of X-ray structure of 157. 122 2.5 NOE data for the photoadducts

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:: ..................................................................................................207 152

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

Creator:: Ruppert, John Fredrick
Resource Type:: Dissertation
Full Text:: epoxidized with basic hydrogen peroxide to afford 152. In another approach, the acetate from 137 was

Synthetic approaches to the tricarbonyl subunit of rapamycin

Creator:: LaMunyon, James B.
Abstract:: Rapamycin (5) was isolated in 1975 from the soil bacteria Streptomyces hygroscopicus and its structure was determined from spectroscopic techniques and an x-ray crystallographic analysis. Although it was initially found to exhibit antibiotic activity, it was subsequently shown to possess potent immunosuppressive activity as well. Three approaches to the synthesis...
Resource Type:: Masters Thesis
Full Text:: (Scheme XXIII). Displacement of 151 with NaI gave the iodide 152 which underwent substitution of the

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:: acetate to yield 4.3 g (50%) of 36: mp 151 - 152 °C; (lit 22 mp 152-153 o C). (+)-erythro-2-Methyl-2,3

Synthetic studies on alkaloids : part I, an approach toward the synthesis of (̳+)-koumine : part II, an approach toward the synthesis of (̳+)-morphine

Creator:: Stappenbeck, Frank
Resource Type:: Dissertation

Natural product synthesis via cyclobutanes : part I, Asymmetric synthesis of (+)-byssochlamic acid, part II, An approach to the nootropic agent huperzine A

Creator:: Kim, Jungchul
Abstract:: PART I. Asymmetric syntheses of both natural (+)- and nonnatural (-)-byssochlamic acid via a [2+2] photoaddition-cycloreversion strategy are described. X-ray crystallographic analysis of the cyclohexylamine salt 99 showed that the structure of the monomethyl ester 100 from esterase hydrolysis of 44 was originally misassigned as 56. The enantiomeric relationship of...
Resource Type:: Dissertation
Full Text:: Conformation of selenoxides 185 and 186. 146 2.7 ORTEP Representation from X-ray structure of 197. 152 2.8

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:: ,3-unsaturated ester 151 to allylic alcohol 152 which underwent Sharpless asymmetric epoxidation to

ScholarsArchive@OSU

Synthetic studies of nonadrides

Synthesis of two subunits of avermectin B1a

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

Total synthesis of (-)-7-epicylindrospermopsin

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

Synthetic approaches to the tricarbonyl subunit of rapamycin

Approaches to the synthesis of methymycin

Synthetic studies on alkaloids : part I, an approach toward the synthesis of (̳+)-koumine : part II, an approach toward the synthesis of (̳+)-morphine

Natural product synthesis via cyclobutanes : part I, Asymmetric synthesis of (+)-byssochlamic acid, part II, An approach to the nootropic agent huperzine A

Studies toward the total synthesis of phorboxazole A

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