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Total Synthesis of Aspidosperma Alkaloids Leuconoxine, Melodinine E and Mersicarpine and Synthetic Studies directed toward the Iboga Alkaloid Ibogaine: Progress directed toward the dimeric Cephalotaxus Alkaloid Cephalancetine C

Creator:: Kim, GilSoo
Abstract:: The first part of this manuscript is about the total synthesis of the aspidosperma alkaloids leuconoxine, melodinine E and mersicarpine. Our synthetic strategy used a radical translocation-conjugate addition cascade to construct the core of the natural product. Specifically, a vinyl radical was generated from the homolysis of the C–I bond...
Resource Type:: Dissertation
Full Text:: : ______________________________________________________ Christopher M. Beaudry The first part of this manuscript is about the total synthesis of the

Total Synthesis of Cephalotaxus Alkaloids and Synthetic Studies toward Bazzanin K

Creator:: Ju, Xuan
Abstract:: Dearomatization reactions exist broadly in biosynthesis and chemical synthesis. The highly functionalized atoms of arenes can be masked by it aromaticity, and upon dearomatization, those reactive atoms can be readily applied to bond formation and further manipulation. The total synthesis of (–)-cephalotaxine and (–)- homoharringtonine is described via an oxidative...
Resource Type:: Dissertation
Full Text:: : ______________________________________________________ Christopher M. Beaudry Dearomatization reactions exist broadly in biosynthesis and chemical

Computational Investigation and Prediction of Mechanisms and Stereocontrol in Complex Organic Reactions

Creator:: Pattawong, Ommidala
Abstract:: Complex organic transformations, such as the addition of pyrrole to ketene using planar chiral organocatalyst (*PPY), the four-component anhydride- Manniach reactions, and the site-selective desymmetrization of meso-1,2-diol, are remarkable synthetic reactions that provide high yield and high selectivity. However, the exact mechanism and origins of stereocontrol for theses synthetic organic...
Resource Type:: Dissertation
Full Text:: in part to the preparation and review of this manuscript. Chapter 3. M. Quamar Salih conducted

Total synthesis of phorboxazole A

Creator:: Lee, Tae Hee
Abstract:: The total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, is described. Both a palladium(II)-mediated and a palladium(II)-catalyzed intramolecular alkoxycarbonylation were used as key steps for the preparation of the two cis-2,6-disubstituted tetrahydropyran rings (C22-C26 and C11-C15) of phorboxazole A. The synthesis used a convergent approach involving...
Resource Type:: Dissertation
Full Text:: Synthesis of Trisubstituted Tetrahydropyran 56………………….….. 15 2.2 Chain Extension : Corey-Enders

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:: method of Corey and Fuchs6, followed by alkylation of the terminal alkyne gave access to 7

Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

Creator:: Li, Yang
Abstract:: Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient...
Resource Type:: Dissertation
Full Text:: ν H H O 1.3 1.4 1.5 O H H O H H H H O + 4 In 1964, Corey and co-workers

A Diels-Alder approach to biaryl synthesis

Creator:: Ashburn, Bradley O.
Abstract:: An expedient approach to the synthesis of a wide range of highly programmable biaryl templates has been accomplished. Utilizing the Diels-Alder [4+2] cycloaddition, a wide range of tri- and tetra-ortho-substituted biaryls have been synthesized in only three to four steps from commercially available materials. We have successfully synthesized entire classes...
Resource Type:: Dissertation
Full Text:: .; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2657. 29. Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K

Expanding the scope of a Diels-Alder approach to biaryl synthesis

Creator:: Schwartz, Johanna Perkins
Abstract:: A Diels-Alder approach to biaryls (DAB) has been applied towards the synthesis of highly substituted, programmable biaryl templates. Tri- and tetra-ortho-substituted biaryls can be produced in just three to four steps from commercially available materials utilizing the Diels-Alder [4+2] cycloaddition. The methods described herein will illustrate the ability of mono...
Resource Type:: Dissertation
Full Text:: ) Corey, E. J.; Weinschenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675

Part I: Total synthesis of marine macrolide amphidinolide F and synthetic studies toward amphidinolide C; Part II: Computational study on proline sulfonamide-catalyzed aldol reaction

Creator:: Mahapatra, Subham
Abstract:: More than 30 members of the diverse amphidinolide family of biologically active macrolides have been isolated over last three decades. From this family, amphidinolides C and F stand among the most complex and densely functionalized affiliates. Recently, we have accomplished the first total synthesis of amphidinolide F. The all-carbon framework...
Resource Type:: Dissertation
Full Text:: amphidinolides: (a) Ishibashi, M.; Kobayashi, J. Heterocycles 1997, 44, 543-572. (b) Chakraborty, T. K.; Das, S

Part I: Total Syntheses of Mandelalide A and Isomandelalide A. Part II: Role of π-Stacking on Sharpless Dihydroxylation of cis-Enynes: Synthetic Studies Toward All Carbon Macrocyclic Mandelalide B

Creator:: Ghosh, Ankan
Abstract:: Part I of this dissertation includes the chronological synthetic background of mandelalide A as well as the synthesis of the C1-C14 glycosylated southern subunit of mandelalide. A key aspect of the synthesis includes a novel silver-catalyzed cyclization (AgCC) of a propargylic benzoate to construct the substituted cis-pyran ring system present...
Resource Type:: Dissertation
Full Text:: sulfide to the corresponding sulfoxide with m-CPBA generated the sugar donor 1.4.7. OTBDPS O OBn

ScholarsArchive@OSU

Total Synthesis of Aspidosperma Alkaloids Leuconoxine, Melodinine E and Mersicarpine and Synthetic Studies directed toward the Iboga Alkaloid Ibogaine: Progress directed toward the dimeric Cephalotaxus Alkaloid Cephalancetine C

Total Synthesis of Cephalotaxus Alkaloids and Synthetic Studies toward Bazzanin K

Computational Investigation and Prediction of Mechanisms and Stereocontrol in Complex Organic Reactions

Total synthesis of phorboxazole A

Studies towards the total synthesis of (-)-kendomycin

Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

A Diels-Alder approach to biaryl synthesis

Expanding the scope of a Diels-Alder approach to biaryl synthesis

Part I: Total synthesis of marine macrolide amphidinolide F and synthetic studies toward amphidinolide C; Part II: Computational study on proline sulfonamide-catalyzed aldol reaction

Part I: Total Syntheses of Mandelalide A and Isomandelalide A. Part II: Role of π-Stacking on Sharpless Dihydroxylation of cis-Enynes: Synthetic Studies Toward All Carbon Macrocyclic Mandelalide B

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