Current Topics in Organic Chemistry
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1 Current Topics in Organic Chemistry Lecture notes: rinner-group.univie.ac.at Scheduled meeting times: Dienstag, :15 12:45 Mittwoch, :15 12:45 Dienstag, :15 12:45 Mittwoch, :15 12:45 Dienstag, :15 12:45 Mittwoch, :15 12:45 Uwe Rinner
2 Tyrosine is an important starting material for a variety of natural products:
3 Phenethylisoquinoline alkaloids: Phenethylisoquinoline alkaloids are biosynthesized in analogy to benzyltetrahydroisoquinoline alkaloids:
4 Biosynthesis of colchicine:
5 Colchicine: Highly toxic natural product isolated from the autumn crocus (Colchicum autumnale). Traditionally used to treat gout and swellings. Used as herbal remedies by ancient cultures (Ancient Egypt 1500 BC); first isolated in 1820 by Pelletier and Caventou Approved to treat gout also used in the treatment of various forms of cancer (inhibits tubulin polymerization)
6 Biological Activity - microtubuli: long, filamentous, tube-shaped protein polymers essentiell in development and maintenance of cell shape, transport of vesicles, in cell signaling, cell division, mitosis composed of α- and β- tubulin heterodimers dynamic polymers
7 Biological Activity - microtubuli: importance in mitosis and cell division makes microtubules as a target for anticancer drugs various binding-sites for antimitotic drugs chemically diverse substances bind to soluble tubulin and/or directly to tubulin in the microtubules inhibition of cell proliferation by acting on the polymerization dynamics of spindle microtubules two groups of microtubule-targeted antimitotic drugs microtubule-destabilizing agents microtubule-stabilizing agents
8 Biological Activity - microtubuli: colchicine binds to tubulin inhibits tubulin poymerization disruption of dynamic equilibrium needed in formation of microtubules from α- and β- tubulin heterodimers Formation of abnormal mitotic spindles results in cell cycle arrests in the M-phase and apoptotic cell death
9 Banwell s synthesis of colchicine:
10 Alternative strategies towards colchicine oxidative phenol couplings:
11 Alternative strategies towards colchicine oxidative phenol couplings:
12 Alternative strategies towards :
13 Tyrosine is an important starting material for a variety of natural products:
14 Amaryllidaceae alkaloids: The great variety of Amaryllidaceae alkaloids can be explained by different coupling protocols of the key intermediate.
15 Amaryllidaceae alkaloids: The biosynthesis of Amaryllidaceae alkaloids starts with the formation of 4 -Omethylnorbelladine from tyrosine and phenylalanine.
16 Amaryllidaceae alkaloids: Only few enzymes have been identified which are responsible for the elaboration of the characteristic carbon frameworks. The carbon frameworks are generated by different phenolic coupling reactions of methylnorbelladine.
17 Amaryllidaceae alkaloids proposed biosynthesis of narciclasine: No enzymes have been identified. The proposed route has been developed after extenive studies with 13C and 14C labeled tyrosine.
18 Amaryllidaceae alkaloids proposed biosynthesis of galantamine:
19 Comparison biosynthesis morphine and galantamine:
20 Amaryllidaceae alkaloids biological activity: Plants of the Amaryllidaceae family have been used extensively by ancient cultures worldwide. Over 30 plants have been reported effective in the primitive treatment of cancer. The chemical investigation of Amaryllidaceae alkaloids began with the isolation of lycorine from Narcissus pseudonarcissus in Isolated in 1984 from Pancratium littorale, pancratistatin was identified to be highly active against several human cancer cell lines. Derivatives of pancratistatin are currently used in clinical trials. Hartwell, J. L. Lloydia 1967, 30, 379. Gerrard, A. W. Pharm. J. 1877, 40, 221.
21 Danishefsky s synthesis of pancratistatin:
22 Danishefsky s synthesis of pancratistatin:
23 Hudlicky s synthesis of pancratistatin:
24 Hudlicky s synthesis of narciclasine:
25 Keck s synthesis of 7-deoxypancratistatin:
26 Keck s synthesis of 7-deoxypancratistatin:
27 Hudlicky/Rinner s synthesis of 7-deoxypancratistatin:
28 Barton and Kirby s synthesis of galantamine:
29 Galantamine served as model substrate for the development of oxidative coupling protocols:
30 Galantamine served as model substrate for the development of oxidative coupling protocols:
31 Thank you for your interest
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