Radical Cascade Reactions

• Research unit: COST
• Project number: C98.0089

Key words (English)

organic synthesis; radical reactions; polycyclizations; asymmetric synthesis; biologically active compounds

Research programs (English)

COST-Action D12 - Organic Transformations: Selective processes and Asymmetric Catalysis

Short description (English)

See abstract

Further information (English)

Full name of research-institution/enterprise: Universität Bern Departement für Chemie und Biochemie

Partners and International Organizations (English)

A, B, CH, CZ, D, DK, E, F, H, I, IRL, N, ROM, S, Sl, UK

Abstract (English)

Within two years, a large research network has been established and fruitful collaborations have been initiated resulting in several common publications as well as an important contribution (7 chapters) to a two volumes book entitled 'Radicals in Organic Synthesis'. Radical cascade reactions involving alkoxyl radicals have been investigated. For the first time, generation of alkoxyl radicals from allylsulfoxides was achieved via a reaction sequence involving a sigmatropic rearrangement followed by a homolytic cleavage of an oxygen-sulfur bond. The alkoxyl radicals were then involved in fragmentation-cyclization processes. Based on this approach, a highly efficient alternative to the anionic oxy-Cope rearrangement has been developed and used for the preparation of the core of phyllantocin, a potent antitumor agent. The cyclization of halooacetals (Ueno-Stork reaction) has been further developed and the core of podophyllotoxin, a naturally occurring lignan with strong antitumoral properties, has been achieved. Based on these results, new strategies for the synthesis of natural products and biologically active compounds are accessible and will be further developed.

References in databases (English)

Swiss Database: COST-DB of the State Secretariat for Education and Research Hallwylstrasse 4 CH-3003 Berne, Switzerland Tel. [phone] Swiss Project-Number: C98.0089