Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Second
The biaryl axis is the joint central structural element of a broad variety of structurally (in particular stereochemically) and biosynthetically interesting as well as pharmacologically promising natural products. The increasing importance of this challen
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Contents I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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1.1. General................................................ 1.1.1. Biaryls- Structural and Biosynthetic Variety. . . . . . . . . . . . . . . . . 1.1.2. Classification. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.1.3. Stereochemistry: Atropisomerism . . . . . . . . . . . . . . . . . . . . . . . . . 1.1.4. Bioactivities of Biaryl Natural Products . . . . . . . . . . . . . . . . . . . . 1.1.5. Regio- and Stcreoselective Biaryl Syntheses . . . . . . . . . . . . . . . . . . 1.2. The Elucidation and Stereochemical Description of the Absolute Configuration at Biaryl Axes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2.1. Stereochemical Descriptors for Biaryl Axes . . . . . . . . . . . . . . . . . . 1.2.2. By Nuclear Magnetic Resonance. . . . . . . . . . . . . . . . . . . . . . . . . . 1.2.3. By X-Ray Structure Analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2.4. By Chiroptical Methods. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1.2.5. By Steglich's Modification of the Horeau Method . . . . . . . . . . . . . 1.2.6. By Total Synthesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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2. Non-Bridged Biaryls . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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2.1. Bi- and Polyphenyls . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2. Dimeric Naphthalene Systems . . . . . . . . . . . . . . . . . . . . . 2.2.1. Simple Binaphthalencs and Binaphthoquinones . . . . 2.2.2. The Pcrylencquinoncs . . . . . . . . . . . . . . . . . . . . . . 2.2.3. Dimeric Pyranonaphthoquinones and -naphthalenes, Binaphtho-)•-pyrones, and Binaphtho-rx-pyrones . . . .
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Dedicated to Prof. Burchard Franck, on the occasion of his 75th birthday Corresponding author; e-mail: bringman(a chemie.uni-wuerzburg.de
G. Bringmann et al., Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products © Springer-Verlag Wien 2001
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G. Bringmann et al. 2.3. Dimeric Anthracencs and Anthraquinones . . . . . . . . . . 2.4. Monomeric 9.1 0-Dihydrophenanthrencs. Dim eric Phenanthrenes. and 9,10-Dihydrophenanthrenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.5. Natural Bicoumarins with Biaryl Axes . . . . . . . . . . . . . . . . . . . . . . . . . 2.6. Biftavonoids and Related Compounds . . . . . . . . . . . . . . . . . . . . . . . . . 2.7. Phenylphenalcnones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.8. Constitutionally U nsymmctric. Cross-Coupled Biaryls with Various Iso- or Heterocyclic Building Blocks. . . . . . . . . . . . . . . . . 2.8.1. 1-Phenylanthraquinones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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