Hybrids of sugars and aromatics: A Pd-catalyzed modular approach to chromans and isochromans

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Erscheinungsjahr:
2010
Medientyp:
Text
Schlagworte:
  • Carbohydrates
  • Domino reactions
  • Chromans
  • Isochromans
  • Palladium
Beschreibung:
  • Chroman and isochroman motifs are widespread elements in natural products and have attracted much attention from a wide area of science including natural product chemistry as well as medicinal and synthetic organic chemistry. Chroman-derived natural products possess a broad array of biological activities such as antimicrobial, antiviral, antiproliferative, sex pheromone, antitumor and central nervous system activity.1 Probably the most prominent example of such a biologically active compound with a chroman core is the vitamin E family [α-tocopherol (1)] (Fig. 1), which consists of eight naturally occurring compounds differing in the aliphatic side chain and the residues of the aromatic core leading to varying biological activity.2 A representative example of a synthetic pharmaceutical agent with a chroman scaffold is cromakalin (2), a potent activator of ATP-dependent potassium channels that is known to induce apoptosis.3 Also a plethora of natural products show the chroman core such as the potent anti-HIV agent daurichromenic acid (3), which was isolated from Rhododendron dauricum ( Fig. 1). Its remarkable EC50 value of 5.67 ng/mL and the therapeutic index (TI) of 3710 encouraged a lot of synthetic organic chemists to establish a total synthesis.4
Lizenz:
  • info:eu-repo/semantics/restrictedAccess
Quellsystem:
Forschungsinformationssystem der UHH

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oai:www.edit.fis.uni-hamburg.de:publications/a01f2f33-96ac-4318-835e-8d06f97e74ea