Index Catalog // ScholarsArchive@OSU

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:: spectroscopy and Jeff Morre for his help with mass spectroscopy. Finally, I would like to thank my parents

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:: Quay, Rodger Kohnert, and Jeff Morre for their friendship and useful discussions. I would like to

Studies toward the total synthesis of (+)-providencin

Creator:: Jana, Somnath
Abstract:: Studies toward the total synthesis of (+)-providencin (1), a highly oxygenated cembranoid dipterpene with a unique bicyclo[12.2.0]hexadecane skeleton and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediates 320 and 332 which contain all of the carbon atoms of 1. In a first generation approach...
Resource Type:: Dissertation
Full Text:: , Professor Rich G. Carter, Professor Paul R. Blakemore, Professor Kevin P. Gable, Professor Janet Tate and

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:: produced by this method in high enantiomeric excess. This protocol was used to synthesize (R)-Montelukast

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:: committee members, Professor Rich G. Carter, Professor Paul R. Blakemore, Professor Kevin P. Gable and

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:: Acid 5: Heveadride 3: Glaucanic Acid 6: Castaneiolide O 7a: Rubratoxin A (R = H, OH) 7b

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:: . RI-IN RI-IN R -CO( CH 2 ) 3 CH COOH NH 2 2 C 00H CH OA c 2 Two major problems arose after

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
Full Text:: 75 to boron trifluoride resulted in a Wagner-Meerwein rearrangement which connected carbons 13 and

Part I. The total synthesis of (±)-cinnamodial and related drimane sesquiterpenes; Part II. Photochemical activation of the carboxyl group via N-Acyl-2-thionothiazolidines

Creator:: Burton, Lester Percy Joseph
Resource Type:: Dissertation
Full Text:: ., the water R 1 1 R1=0Ac' R2=0H 2 R1 =R2=H 3 R1 =11, R2=0H CHO 12 4 pepper, and several names

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:: , Paul R. Blakemore, Cindy Browder, Rich G. Carter, Bobby Chow, Jorg Deerberg, Nicholas E. Drapela, Uwe

ScholarsArchive@OSU

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

Total synthesis of phorboxazole A

Studies toward the total synthesis of (+)-providencin

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

Studies toward the total synthesis of sanglifehrin A

Synthetic studies of nonadrides

Approaches to the synthesis of penicillin

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

Part I. The total synthesis of (±)-cinnamodial and related drimane sesquiterpenes; Part II. Photochemical activation of the carboxyl group via N-Acyl-2-thionothiazolidines

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

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