Font Size: a A A

Alkaloid synthesis using N-acylpyridinium salts as building blocks: Progress towards the total synthesis of (-)-FR901483 and synthesis of novel polyheterocyclic compounds

Posted on:2004-12-12Degree:Ph.DType:Thesis
University:North Carolina State UniversityCandidate:Gotchev, Dimitar BorissovFull Text:PDF
GTID:2461390011975733Subject:Chemistry
Abstract/Summary:
A study directed toward the total synthesis of the potent immunosuppressant (−)FR901483 was examined. Three approaches to the tricyclic core of the targeted molecule were investigated, utilizing Grignard addition to an N-acylpyridinium salt and quaternary center formation as the key synthetic steps. In the first route, a pivotal keto-aldehyde intermediate was needed to study an intramolecular pinacol coupling approach to the backbone of the title compound. In the second and third generation synthetic designs, an intramolecular 6-exo-tet epoxide opening was envisioned as a means of generating the azabicyclo ring system of the target.; Three novel polyheterocyclic ketones were synthesized in a flexible manner in search for an asymmetric epoxidation catalyst of unfunctionalized trans-alkenes. The targeted compounds were derived via a regiospecific alkylation of 5-hydroxy-2-methylpyridine, followed by functional group manipulation and nitrogen atom cyclization.
Keywords/Search Tags:Synthesis
Related items
1 Green chemistry in pyrrole synthesis. I. Solvent effect in Barton-Zard pyrrole synthesis: An improved synthesis of 3,4-dialkyl-1H-pyrrole-2-carboxylates. II. A novel route for the synthesis of pharmaceutically important pyrrole derivatives
2 Part I: Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis Part II: Studies toward a synthesis of the antibiotic platensimycin
3 Manganese(III)-based oxidative cyclizations: Formal synthesis of 15-acetoxypallescensin A. Synthesis of hindered guanidines. Completion of the total synthesis of martinellic acid
4 Synthesis, Characterization And Luminescence Properties Of Environmental Functional Material β-NaYF4 Doped With Rare Earth
5 Part I: The total synthesis of (+/-)-securinine and (+/-)-allosecurinine and synthetic strategies for a second generation synthesis of the securinega alkaloids and Part II: The use of (+)-K252a in the semi-synthesis of indolocarbazole natural products and
6 New methods and strategies for heterocycle synthesis: Progress toward the total synthesis of upenamide and the total synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB
7 Synthesis of side chain-modified iodothyronines. Synthesis and structure-activity relationships (SARS) of galanthamine derivatives. Total synthesis of (+)-valyldetoxinine. Synthesis and mechanism of cyclic acetal and ketal formation in pentono-1,4-lactone
8 The application of asymmetric catalysis to the synthesis of natural products: A total synthesis of (-)-tubulosine, progress towards a total synthesis of (+)-reserpine, and a total synthesis of (+)-peloruside A
9 Cyclobutanes in organic synthesis: Lewis acid-promoted ketene-alkene [2+2] cycloadditions, total synthesis of gracilioether F, and collaborative total synthesis of hippolachnin A
10 A ring-closing metathesis/Diels-Alder approach to the synthesis of the eunicellin diterpenes: Application to the total synthesis of ophirin B and partial synthesis of astrogorgin