Biosynthesis of algae pheromones. 4. pericyclic-reactions in nature - 
spontaneous cope rearrangement inactivates algae pheromones

Boland, W.; Pohnert, G.; Maier, I.

doi:10.1002/anie.199516021

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Biosynthesis of algae pheromones. 4. pericyclic-reactions in nature - spontaneous cope rearrangement inactivates algae pheromones

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Boland, W., Pohnert, G., & Maier, I. (1995). Biosynthesis of algae pheromones. 4. pericyclic-reactions in nature - spontaneous cope rearrangement inactivates algae pheromones. Angewandte Chemie International Edition, 34(15), 1602-1604. doi:10.1002/anie.199516021.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0012-9F4E-C

Abstract

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.