Financial support from GlaxoSmithKline, Pfizer, and the EPSRC is gratefully acknowledged. Dr. Mark Bunnage (Pfizer) is thanked for helpful discussions.
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Communication
Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration†
Article first published online: 18 MAY 2005
DOI: 10.1002/anie.200500466
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Harrowven, D. C., Woodcock, T. and Howes, P. D. (2005), Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration. Angew. Chem. Int. Ed., 44: 3899–3901. doi: 10.1002/anie.200500466
- †
Publication History
- Issue published online: 10 JUN 2005
- Article first published online: 18 MAY 2005
- Manuscript Received: 7 FEB 2005
Keywords:
- arenes;
- macrocycles;
- radical reactions;
- ring contraction;
- total synthesis
A transannular ring contraction induced by the addition of an aryl radical intermediate to a proximal arene facilitated the construction of the highly strained macrocyclic core of cavicularin (1). The precursor, an iodinated derivative of another natural product, riccardin C, was prepared from four commercially available arenes in a highly convergent sequence.