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

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.

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BOL000.pdf (Publisher version), 338KB
 
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Boland, W.1, Author           
Pohnert, G.1, Author           
Maier, I.1, Author           
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1External Organization, ou_persistent22              

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 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.

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 Dates: 1995
 Publication Status: Published in print
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 Identifiers: Other: BOL000
DOI: 10.1002/anie.199516021
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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 34 (15) Sequence Number: - Start / End Page: 1602 - 1604 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851