Strigolactone Analogues with a D‐Ring Modified at C‐2

Strigolactones (SLs) are important new plant hormones that receive much attention in current plant science. SLs are produced by many plants and are exuded by the root system. SLs are, amongst others, germination stimulants for seed of parasitic weeds. Naturally occurring SLs invariably contain three annelated rings, the ABC‐scaffold, connected to a butenolide (the D‐ring) via an enol ether unit. The synthesis of natural SLs requires many steps, therefore there is a continuous search for SL analogues with a simpler structure but with retention of bioactivity. In this study modified D‐ring variants are investigated, especially analogues having a methyl group at C‐2 instead of a hydrogen. For these analogues the ABC‐scaffolds of GR24 and Nijmegen‐1 were used. The coupling reaction proceeds profoundly better with chlorobutenolides than with the corresponding bromides. Bioassays reveal that the introduction an extra methyl at C‐2 does not influence the germination activity, which is relevant for gaining insight in the mode of action of SLs.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
Strigolactone Analogues with a D‐Ring Modified at C‐2 ; volume:2016 ; number:21 ; year:2016 ; pages:3495-3499 ; extent:5
European journal of organic chemistry ; 2016, Heft 21 (2016), 3495-3499 (gesamt 5)

Urheber
Mwakaboko, Alinanuswe S.
Zwanenburg, Binne

DOI
10.1002/ejoc.201600576
URN
urn:nbn:de:101:1-2022111506392824525966
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:30 MESZ

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Beteiligte

  • Mwakaboko, Alinanuswe S.
  • Zwanenburg, Binne

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