Asymmetric One-Pot Transformation of Isoflavones to Pterocarpans and Its Application in Phytoalexin Synthesis
Peter Metz reports a one-pot transformation of isoflavones to pterocarpans and its further application.
Phytoalexins are structurally diverse, low-molecular-weight secondary metabolites that are produced ex novo in appreciable amounts by plants following a pathogenic attack. These antimicrobials may be isolated from stressed soy plants and, owing to their interesting biological properties, have attracted the attention of many research groups in recent years. Some phytoalexins have shown capacity for selectively modulating the activity of the oestrogen receptor, which plays an important role in the growth of oestrogen-related cancers, e.g. mammary carcinoma or ovarian cancer. Furthermore, their anti-inflammatory and anti-cholesterolemic activity, as well as further health-promoting effects, are under investigation all over the world.
The development of a concise catalytic access to structurally defined phytoalexins, such as the enantiopure pterocarpans glyceollin I and glyceollin II, is an important entry to these compounds and was the driving force of the research described in a paper recently published by Professor Peter Metz and Dr. Philipp Ciesielski (Technische Universität Dresden, Germany).