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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:: ketone and a catalytic amount of triethylamine (14, 15, 16, 17) gave the Michael adduct (18) 35 (98

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:: sulfa-Michael addition (SMA) of thiols to acyclic a,(3- unsaturated ketones. I3-Thiaketones are

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:: , Asymmetric synthesis of (+)-byssochlamic acid, part II, An approach to the nootropic agent huperzine A AN

Synthesis of marine natural products. part I, Cryptophycins-1, -3, -4, -24, and -29, part II, Polycavernoside A

Creator:: Robarge, Lonnie A.
Resource Type:: Dissertation
Full Text:: reaction in the formation of vinyl bromide 127 was Michael addition of a suitably functionalized hydroxy

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 C1-C32 MACROLACTONE OF PHORBOXAZOLE A AN

Approaches toward the asymmetric synthesis of pillaromycin A

Creator:: Nolen, Ernest G.
Resource Type:: Dissertation
Full Text:: required formation of an o-toluate anion 20, a Michael reaction of this anion with a cyclohexenone

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:: :_____________________________________________________ James D. White Studies towards the total synthesis of (−)-kendomycin (1), a bacterial

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:: hetero-Michael addition that gave substituted tetrahydropyran 27 preferentially in a 4:1 diastereomeric

Part I : synthesis of azetidin-2-ones from pyrazolidin-3-ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506

Creator:: Toske, Steven Gerald
Resource Type:: Dissertation
Full Text:: -ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506 AN ABSTRACT OF THE THESIS OF

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:: The isolation and structure of leptosphaerin : a metabolite

ScholarsArchive@OSU

The synthesis of trisporic acids

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

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

Synthesis of marine natural products. part I, Cryptophycins-1, -3, -4, -24, and -29, part II, Polycavernoside A

Total synthesis of phorboxazole A

Approaches toward the asymmetric synthesis of pillaromycin A

Studies towards the total synthesis of (-)-kendomycin

Studies toward the total synthesis of phorboxazole A

Part I : synthesis of azetidin-2-ones from pyrazolidin-3-ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506

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

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