EAN: 9783211836538

FORTSCHRITTE DER CHEMIE ORGANISCHER NATURSTOFFE...

1. 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.

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