An Efficient Enantioselective Synthesis of Strigolactones with a Palladium-Catalyzed Asymmetric Coupling as the Key Step

Reizelman, Anat; Zwanenburg, B.

doi:10.1002/1099-0690(200203)2002:5<810::aid-ejoc810>3.0.co;2-u

Cited by 22 publications

(20 citation statements)

References 35 publications

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“…The present authors have developed some methodologies that can be helpful in controlling the stereochemistry in a synthesis sequence 19, 20, 43, 45, 47. An example is an elegant method for installing the desired stereochemistry during coupling with the D‐ring by a palladium‐mediated asymmetric synthesis using the Trost ligand 84. For the introduction of substituents in the AB part of the strigolactones, it is attractive to use biomimetic conversions, i.e.…”

Section: Future Challenges In Synthesismentioning

confidence: 99%

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

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220

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The structures of naturally occurring germination stimulants for seeds of the parasitic weeds Striga spp. and Orobanche spp. are described. The bioactiphore in this strigolactone family of stimulants is deduced from a structure-activity relationship and shown to reside in the CD part of the stimulant molecule. A molecular mechanism for the initial stages of seed germination is proposed. The influence of stereochemistry on the stimulant activity is significant. Combining this molecular information leads to a model for the design of synthetic strigolactones. Nijmegen-1 is a typical example of a highly active, newly designed synthetic stimulant. The occurrence of natural stimulants not belonging to the strigolactone family, such as cotylenin and parthenolide, is briefly described. The biosynthesis of natural strigolactones from beta-carotene is analysed in terms of isolated and predicted stimulants. This scheme will be helpful in the search for new strigolactones from root exudates. Protein fishing experiments to isolate and characterise the receptor protein using biotin-labelled GR 24 are described. A receptor protein of 60 kD was identified by this method. Nijmegen-1 has been tested as a suicidal germination agent in field trials on tobacco infested by Orobanche ramosa L. The preliminary results are highly rewarding. Finally, some future challenges in synthesis are described. These include synthesising new natural and synthetic stimulants and establishing the molecular connection between strigolactones as germination stimulants, as the branching factor for arbuscular mycorrhizal fungi and as an inhibitor of shoot branching.

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Section: Future Challenges In Synthesismentioning

confidence: 99%

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Zwanenburg

Mwakaboko

Reizelman

et al. 2009

Pest Management Science

Self Cite

220

192

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“…The second method is based on a Pd‐catalysed asymmetric coupling of the D‐ring using Trost's DACH‐phenyl ligand as chiral ligand. This methodology has been used for the enantiocontrolled synthesis of Nijmegen‐1, GR7 and GR24 (Scheme ) …”

Section: Total Synthesis Of Natural Slsmentioning

confidence: 99%

“…This methodology has been used for the enantiocontrolled synthesis of Nijmegen-1, GR7 and GR24 (Scheme 2). 16 For GR7 and GR24, the coupling results in a 1:1 mixture of two epimers having the same stereochemistry at C-2 ′ . introduced prior to the ring closure of the C-ring in two steps.…”

Section: Instalment Of the Correct Stereochemistry At C-2 ′mentioning

confidence: 99%

Synthesis of strigolactones, a strategic account

Zwanenburg

Zeljković

Pospíšil

2015

Pest Management Science

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Strigolactones (SLs) constitute a new class of plant hormones that have received growing interest in recent years. They firstly became known as signalling molecules for host recognition by parasitic plants, and for symbiosis of plants with arbuscular mycorrhizal fungi. Furthermore, they are involved in numerous physiological processes in plants, such as the regulation of plant architecture and the response to abiotic factors. SLs are produced by plants in extremely low quantities, and they may be unstable during the purification process. Therefore, their total synthesis is highly relevant for confirming the structures assigned on the basis of spectroscopic and other physical data. A second important theme in SL research is the design and synthesis of SL analogues that have a simplified structure while still featuring the essential bioproperties. This review summarises the strategy and synthesis of naturally occurring SLs, and the design and synthesis of SL analogues with appreciable bioactivity.

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“…First reported in 1981, [8] (AE)-GR24 has been the target of several syntheses but is still commonly employed as a racemic mixture of diastereomers. [9][10][11][12][13] The importance of employing single enantiomers has been underscored by the recent discovery that GR24 isomers with the absolute stereochemistry corresponding to natural (þ)-strigol (1) and (À)-orobanchol (4), exert different biological effects. [14] As such, we recently reported a concise enantioselective route to any stereoisomer of GR24.…”

Section: Introductionmentioning

confidence: 99%

Chemistry of the Synthetic Strigolactone Mimic GR24

2015

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An Efficient Enantioselective Synthesis of Strigolactones with a Palladium-Catalyzed Asymmetric Coupling as the Key Step

Abstract: An efficient enantioselective methodology for the preparation of the strigolactones GR7, GR24 and Nijmegen-1 based on palladium-catalyzed asymmetric coupling has been developed. The products are obtained in good yield and high

Cited by 22 publications

References 35 publications

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Structure and function of natural and synthetic signalling molecules in parasitic weed germination

Synthesis of strigolactones, a strategic account

Chemistry of the Synthetic Strigolactone Mimic GR24

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