Biosynthesis of Algae Pheromones, Part 4. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We thank Prof. Dr. D. G. Müller (Universität Konstanz) for his support. Part 3: ref. .
Article first published online: 22 DEC 2003
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 34, Issue 15, pages 1602–1604, August 18, 1995
How to Cite
Boland, W., Pohnert, G. and Maier, I. (1995), Pericyclic Reactions in Nature: Spontaneous Cope Rearrangement Inactivates Algae Pheromones. Angew. Chem. Int. Ed. Engl., 34: 1602–1604. doi: 10.1002/anie.199516021
Dedicated to Professor Hans-Jürgen Bestmann on the occasion of his 70th birthday
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 4 FEB 1995
- Cope rearrangements;
- pericyclic reactions;
A pheromone roughly 100 times more effective than cyclohepta-1,4-diene 2 (R = C2H5, ectocarpene) is its biosynthetic precursor 1. This thermally labile cis-disubstituted cyclopropane is the actual signaling agent of the marine brown algae Ectocarpus siliculosus. The [3,3]sigmatropic rearrangement of 1 giving 2 (t1/2 = 21 min at 18°C) is the fastest known reaction for the spontaneous inactivation of a pheromone.