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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:: . 31 (3H, s), 1. 01 (3H, t, J=7 Hz); mass spectrum m/e 198. 088 (M+, calc for C10 H1404 198. 089). 4

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:: , 1640cm-1; 1H NMR (400MHz, CDC13) 8 7.51 (2H, m), 7.39 (3H, m), 6.45 (1H, d, J=6.01), 5.67 (1H, s), 5.02

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:: NMR (400 MHz, CDCI3) 0.90 (3H, t, J= 7Hz), 1.35 (3H, m), 1.80 (1H, m), 2.21 (1H, dd, J= 2, 15 Hz

Synthetic studies on marine natural products : Part 1. Synthesis of the sesquiterpenoid dihydropallescensin D via manganese(III)- mediated carbocyclization. Part 2. Approaches toward the synthesis of prianosin and discorhabdin alkaloids

Creator:: Yager, Kraig M.
Resource Type:: Dissertation
Full Text:: Redacted for Privacy To the memory of my mother Kathleen M. J. Yager Acknowledgements I would like

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:: , 2371. (e) Schmitkamp; M.; Chen, D.; Leitner,W.; Klankermayer, J.; Francio, G. Chem. Commun. 2007

Approaches to the synthesis of polyketides. Vermiculine

Creator:: Kirkemo, Curtis Lee
Abstract:: An approach to the generation of polyketides was investigated, which involved ozonolysis of 6, 7 cyclopenteno -1> 4, 5, 8 -tetrahydromethoxy- 3-methylnaphthalene (26), to produce what is believed to be polyketide 27. Compound 26 was formed by the following sequence: Die ls -Alder addition of 1, 2 -dim.ethylenecyclopentane and 2...
Resource Type:: Dissertation
Full Text:: the resulting product (98) gave diester 99. Epoxidation of 99 with m-chloroperbenzoic acid yielded

An approach toward the synthesis of euonyminol and cathedulin K- 19

Creator:: Shin, Hyunik
Abstract:: A synthetic approach toward the two major fragments of cathedulin K-19, euonyminol (4) and dimethyl cathate (69), was investigated. Synthesis of dimethyl cathate was accomplished in 3 steps starting from 73. Efforts directed towards the synthesis of euonyminol, a highly oxygenated dihydroagarofuran sesquiterpene, was advanced to a stage in which...
Resource Type:: Dissertation
Full Text:: latter was epoxidized stereoselectively by m-chloroperbenzoic acid to yield 91. Introduction of an

Approaches toward the asymmetric synthesis of pillaromycin A

Creator:: Nolen, Ernest G.
Resource Type:: Dissertation
Full Text:: - plicity integral dq 1H dd 1H dd 1H m 2H q 1H dt 1H s 3H ddd 1H d 3H d 3H J 4,7 2,4

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:: (m, IH), 5.10 (m, 2H), 4.45(s, 2H), 3.80 (S, 3H), 3.57 (m, 2H), 3.44(dd, IH, J= 7.1, 9.2 Hz), 3.30

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

ScholarsArchive@OSU

The synthesis of trisporic acids

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

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

Synthetic studies on marine natural products : Part 1. Synthesis of the sesquiterpenoid dihydropallescensin D via manganese(III)- mediated carbocyclization. Part 2. Approaches toward the synthesis of prianosin and discorhabdin alkaloids

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

Approaches to the synthesis of polyketides. Vermiculine

An approach toward the synthesis of euonyminol and cathedulin K- 19

Approaches toward the asymmetric synthesis of pillaromycin A

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

Studies toward the total synthesis of phorboxazole A

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