Dissertation > Excellent graduate degree dissertation topics show

Studies on the Total Synthesis of Rocaglamide

Author: ZhengJie
Tutor: SunLiangDong
School: Tianjin University
Course: Organic Chemistry
Keywords: Rocaglamide Insecticidal activity Anti-tumor activity Total synthesis Nazarov cyclization
CLC: O626.11
Type: Master's thesis
Year: 2009
Downloads: 29
Quote: 0
Read: Download Dissertation

Abstract


The attempted total synthesis of natural product-Rocaglamide and its analogues was described in the dissertation. Isolated from the roots and stems of Aglaia elliptifolia (Meliace), Rocaglamide has been proved to be of anti-tumor, anti-leukemic and insecticidal activities. Its structure, determined by single-crystal X-ray analysis, was reported in 1982 by King etc. It is a great challenge to synthesize the tricyclic core structure of Cyclopenta[b]benzofuran skeleton bearing a highly functionalized cyclopentane moiety with five stereogenic centers. The advantages of our short synthesis route to Rocaglamide are utilizing inexpensive reagents, conducting under mild reaction conditions and also obtaining the product in very high stereoselectivity. First, 6-Hydroxy-2,4-Dimethoxylbenzaldehyde was prepared from anhydrous phloroglucinol via Vilsmeier-Hack reaction and dimethylation. The product reacted with 4-methoxyphenylpropan-1-one in the presence of dry HCl gas to give the flavylium salt. The benzofuran product was obtained after oxidation by H2O2. There synthetic routes were designed based on this important intermediate.In the first route, we tried different reaction conditions of Baeyer-Villiger Oxidation to the former structure of the target compound. Though it is unsuccessful, we find a new method to synthesize another former structure of the target compound.Some preliminary research has been conducted favourably in the second route. An efficient method to synthesize of 2-(4-methoxyphenyl)-3-cinnamoylbenzofuran and the product is very probable to be a cycle compound, so the preparation of Intermediate Three is very hopeful.In the third route, we have managed to complete the synthesis of the 2-(4-methoxyphenyl)-3-(3-phenyl-1-chloropropenyl)benzofuran. In further research, the main task is to find a really suitable condition for the synthesis of 2-(4-methoxyphenyl)-3-(3-phenyl-1-propynyl)benzofuran.

Related Dissertations

  1. Atovaquone analogues Design, Synthesis and antitumor activity of,R914
  2. Insecticidal Activities of Recombinant CryIAc Protein from Bacillus Thuringiensis and Solid Fermentation Products from Aspergillus Terreus PNR2,S476.1
  3. Avocados Persea americana contain long-chain alkylene triol total synthesis and absolute configuration determined,O621.3
  4. Extraction, Isolation and Identification of the Metabolites from Plants of Elsholtzia Splendens and Sedum Alfredii Hance Post-phytoremediation,X173
  5. Studies on Synthesis and Anticancer Activity of Some Schiff Bases,R730.5
  6. Investigation on Hydroxycamptothecin Loaded Acid-labile Polymeric Nanoparticles,TQ460.1
  7. Synthesis and Insecticidal Activities of 2α/β-Bromo-4α-Alkyloxy-Podophyllotoxin Derivatives,S482.3
  8. Cashew nut shell oil and preparation of insecticidal activity of antibacterial,S436.64
  9. Study on the Optimization of the Fermentation Media of the Highly-yielding Strain Cordyceps Militaris and the Anticancer Activity of Its Polysaccharide,S567.35
  10. Modification of Resveratrol and Antitumor Activity of Its Derivatives,R285
  11. Study on the Insecticidal Activities of Neem Leaves and Active Components Against Oxya Chinensis,R284.2
  12. Pharmacognostic Study on Pollicipes Mitella,R282.74
  13. Preliminary Study on Endophytic Fungus in Euonymus Microcarpus (Oliv.) Spraggue,S182
  14. Synthesis and Biologic Activity of Anthranilic Diamides Derivatives Target at Insect Ryanodine Receptor,S482.3
  15. Synthesis and Biological Activity of Oxime Ether and Oximino Phosphorothioates Containing 1H-1,2,4-triazole and N-(Aryloxyacetyl), N’-[(Z)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl Cyclopropanecarbonyl]Hydrazines,TQ450.2
  16. Isolation of Ginkgolic Acid Monomers and Killing Activity to Pathogen and Dactylogyrus of Fish,S948
  17. The Toxicity of Research on the Edible Fungi Pest Lycoriella Pleuroti of Macrofungi,S436.46
  18. Amines Changchun alkaloids Iraq spinach Ibogamine synthesis and leaves one hundred bases synthesis,R284.1
  19. Studies on Chemical Constituents and Anticancer Activity from Cremastra Appendiculata,R285
  20. Endophyte CPCC480435 preliminary study of bioactive substances,R284
  21. Marine fungus Y19-07 secondary metabolites,R915

CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds > Five heterocycles containing a single different atoms > Oxa -mao ( furans) family
© 2012 www.DissertationTopic.Net  Mobile