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Chiral synthesis of monic acid C

Creator:: Theramongkol, Parinya
Abstract:: Bromoalkoxylation of dihydropyran with bromine and 1-borneol, followed by dehydrobromination and epoxidation, afforded trans-2-1- bornyloxy-3,4-epoxytetrahydropyran as a major product. This was treated with sodium phenylselenide to give a 1:1 mixture of (2R,3R,4R)- 2-1-bornyloxy-3-hydroxy-4-phenylselenotetrahydropyran and its (2S,3S, 4S) diastereomer. Elimination of the selenoxide, derived from oxidation of the former with hydrogen...
Resource Type:: Dissertation
Full Text:: Pseudomonas fluorescens (NCIB 10586). These are pseudomonic acid A (6),7 B (7),8 C (8),9 and D (9).10

Synthetic studies on the macrolide antibiotic rutamycin B

Creator:: Wang, Shan
Resource Type:: Dissertation
Full Text:: CH2 Oligomycin B Me H OH CO Oligomycin C Me H H CH2 Oligomycin E Me OH OH CO Rutamycin A H H OH

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

Creator:: Ruppert, John Fredrick
Resource Type:: Dissertation
Full Text:: Cyclopentanone 95 50 b 93 CH 2 COOEt (17) OH Cyclohexanone 93 56d 85 CH COOEt (18) Benzaldehyde 2 C H CH

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:: structures for DIANANE (26; A (side view)) and cis-2,5-diaminobicyclo[2.2.2]octane (34; B (side view) and C

Synthetic studies n bioactive natural products. Part I, An approach towards the nootrophic agent huperzine A. Part II, Synthesis of the tricarbonyl subunit of rapamycin

Creator:: Jeffrey, Scott C.
Resource Type:: Dissertation
Full Text:: rapamycin AN ABSTRACT OF THE DISSERTATION OF Scott C. Jeffrey for the degree of Doctor of Philosophy in

Approaches to the total synthesis of verrucarol

Creator:: Hill, David E. (David Edwin) 1954-
Abstract:: Verrucarol is the sesquiterpene portion of a number of macrocyclic di- and triesters of potential medicinal importance. In this study, a novel approach to the synthesis of this fungal metabolite is presented. An A-B-C route was investigated in which C-3 and C-4 of the C-ring were emplaced using a [2+2]...
Resource Type:: Dissertation
Full Text:: fungal metabolite is presented. An A-B-C route was investigated in which C-3 and C-4 of the C-ring were

Synthesis of epothilones and epothilone analogues

Creator:: Sundermann, Kurt F.
Abstract:: A convergent synthesis of epothilone B that generates all seven of its asymmetric centers in a completely stereoselective fashion has been completed. Key reactions include an anti-Felkin aldol condensation to set the C6 and C7 stereochemistry, a directed α-hydroxylation to install the C15 (S)-hydroxyl substituent, and a Wittig condensation to...
Resource Type:: Dissertation
Full Text:: B (2) developed by Nicolaou. OH OTBS 5 steps 177 TBSOfJ'V5 SnBu3 Sn9r4 />c- 0 OSEM 62% SEMO

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:: considered to be the 1 R , R2 0 9-cis-TRISPORIC ACID B Ri W H, R2 =01-1 9-c is- TRISPORIC ACID C 3 4 5

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:: retrosynthetically into three segments A, B and C (Figure 5). The spiro-ketal unit (segment C) of both Figure 5

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:: cyclization that provided tetracyclic ketone 5.86 containing rings A, B, C and D of vindorosine. A

ScholarsArchive@OSU

Chiral synthesis of monic acid C

Synthetic studies on the macrolide antibiotic rutamycin B

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

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

Synthetic studies n bioactive natural products. Part I, An approach towards the nootrophic agent huperzine A. Part II, Synthesis of the tricarbonyl subunit of rapamycin

Approaches to the total synthesis of verrucarol

Synthesis of epothilones and epothilone analogues

The synthesis of trisporic acids

Synthesis of two subunits of avermectin B1a

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

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