Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

1. General 1. 1. 1. Biaryls-Structural and Biosynthetic Variety The biaryl axis is the joint central structural element of a broad variety of structurally (in particular stereochemically) and biosynthetically inter esting as well as pharmacologically promising natural products. The increasing importance of this challenging class of secondary metabolites, its widespread occurrence, its pharmacological implications, and, in particular, the phenomenon of axial chirality, have so far been largely underestimated, if not neglected. This is reflected by the fact that there is as yet no true comprehensive review on naturally occurring biaryls in the literature. By this article, we do not intend to provide such a fully comprehensive review, but still want to draw the attention of the scientific community on the manifold rewarding facets of this exciting class of natural products, which is rapidly growing now, with more and more sophisticated analytical and synthetic tools becoming available. Natural biaryls occur far more frequently than initially assumed, among them constitutionally symmetric, simple dimeric monoterpenoid biphenyls like I (I) (see Fig. 1), binaphthalenes like (-)-gossypol (2) (2), bianthraquinones like skyrin (3) (3-7), and biaryls with annelated heterocyclic rings like bismurrayafoline-B (4) (8) and desertorin A (Sa) (9, 10), which is-although built up from a single monomeric precursor -constitutionally unsymmetric.

First review that covers this important and rapidly growing class of natural products, as a whole Well designed schemes and figures Picturesque photos

Klappentext

The book gives a hitherto unavailable overview on a huge class of - so far largely neglected - natural products, characterized by one common structural element, a biaryl axis. Covering more than 1300 references, this review mainly focuses on the isolation of these compounds from natural sources, their structural elucidation with special regard to the biaryl axis as a possible stereoelement, their biological activities, and on their biosynthetic origin. Informative summaries on stereochemical aspects connected to a stereogenic axis and on the determination of axial configurations are given, as well as some selected examples out of atroposelective total syntheses. Never has this subject been addressed in such a detailed way, especially not concerning the great variety of different structural subgroups. This book should find the way to the library of any scientist working in the field of natural product, since it provides data on an overwhelming number of naturally occurring substances.

Inhalt
Contents Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologicall Intriguing Secondary Metabolites (G. Bringmann, C. Günther, M. Ochse, O. Schupp, S. Tasler) Introduction General The Elucidation and Stereochemical Description of the Absolute Configuration at Biaryl Axes Non-Bridged Biaryls Bi- and Polyphenyls Dimeric Naphthalene Systems Dimeric Anthracenes and Anthraquinones Monomeric 9,10-Dihydrophenanthrenes, Dimeric Phenanthrenes, and 9,10-Dihydrophenanthrenes Natural Bicoumarins with Biaryl Axes Biflavonoids and Related Compounds Phenylphenalenones Constitutionally Unsymmetric, Cross-Coupled Biaryls With Various Iso-or Heterocyclic Building Blocks Arylnaphthalene Lignans Naphthylisoquinoline Alkaloids Unbridged Biaryl Alkaloids Bridged Biaryls Lactone-Bridged Biaryls The Dibenzocyclooctadiene Lignans Macrocyclic Biphenyls Bridged Biaryl Alkaloids Biaryl Glycopeptides and Other Cyclic Peptides with a Biphenyl Unit