Synthesis of 7-Oxo-5-deoxystrigol, a 7-Oxygenated Strigolactone Analog

Tanaka, Masashi; Sugimoto, Yukihiro; Kuse, Masaki; Takikawa, Hirosato

doi:10.1271/bbb.130020

Cited by 7 publications

(4 citation statements)

References 14 publications

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“…Racemic [6′-D]-5DS isomers (rac-d 1 -1 and rac-d 1 -2) and sorgomol isomers, 8-epi-sorgomol (7), 2′,8-bisepi-sorgomol (8), 2′-episorgomol (9), and 7-hydroxy-5DS (10), were prepared using the method reported previously. 11,22) Racemic [2-13 C,6′-D]-5DS (1a/1b) and its diastereomer, [2-13 C,6′-D]-4DO (2a/2b), were prepared according to the method reported previously. 23 13 C,6′-D]-ent-4DO (2b) were eluted at 16.9 and 19.9 min, respectively.…”

Section: Chemicalsmentioning

confidence: 99%

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

et al. 2018

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The bioconversion of 5-deoxystrigol (5DS) and 4-deoxyorobanchol (4DO), the simplest canonical strigolactones (SLs), into monohydroxylated SLs such as strigol, sorgomol and orobanchol was confirmed by administering of stable isotope-labeled substrates to hydroponically grown plants. Liquid chromatography-mass spectrometry analyses established that 5DS was stereoselectively converted into strigol and sorgomol by cotton (Gossypium hirsutum) and Chinese milk vetch (Astragalus sinicus), respectively. 4DO was converted into orobanchol by rice (Oryza sativa). However, the red bell pepper (Capsicum annuum), red clover (Trifolium pratense), and pea (Pisum sativum) negligibly converted 4DO into orobanchol. The red bell pepper converted ent-4DO into 2′,8-bisepi-sorgomol. These results suggest that some plants generate orobanchol without passing through 4DO.

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Section: Chemicalsmentioning

confidence: 99%

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

et al. 2018

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“…The strategy outlined above is generally applicable. This is demonstrated by the total synthesis of 7‐oxo‐5‐deoxystrigol . Once the starting material with an oxo group adjacent to the gem dimethyl has been obtained from 2,2‐dimethylcyclohexane‐1,3‐dione, the usual sequence of preparing the ABC scaffold and attaching the D‐ring was followed (Scheme ).…”

Section: Total Synthesis Of Natural Slsmentioning

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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“…In the same way, some plants species synthetize orobanchol by bioconversion of 4-deoxyorobanchol, although other species would synthetize it from another compound. Tanaka et al (2013) reported a synthetic strategy to obtain the analogue 7-oxo-5-deoxystrigol in 11 steps from 2,2-dimethylcyclohexane-1,3-dione (Scheme 27). This route starts with protection of one of the ketone groups, which is then transformed into a dienone by way of Grignard and oxidation reactions.…”

Section: Strigol Orobanchol and Sorgomol Familiesmentioning

confidence: 99%

Strategies for the synthesis of canonical, non-canonical and analogues of strigolactones, and evaluation of their parasitic weed germination activity

et al. 2022

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Strigolactones (SLs) are natural products with promising applications as agrochemicals to prevent infestation with parasitic weeds due to their ability to trigger seed germination. However, their use is still limited because of the low yields in which they are isolated from natural sources. As such, numerous studies have led to strategies for obtaining them, and various structural analogues, by organic synthesis. These analogues have focused attention on the study of SLs, as some of them are easier to synthesize and possess enhanced properties, such as the level of bioactivity. This review provides an overview of the synthesis of SLs, subsequently focusing on the production of analogues with the canonical structure. The germinating activity of the compounds is also described herein, with positive effects on different species of the problematic genera Striga, Orobanche and Phelipanche having been found. The highly active analogue GR24 is currently the most widely studied in the literature, and relevant structural-activity relationships have been proposed as a result of the study of derivatives functionalized in different positions. Analogues based on other natural SLs such as strigol and orobanchol have also been developed, as have some novel canonical SLs derived from eudesmanolide or guaianolide sesquiterpene lactones. This review aims to provide useful information for the development of bioactive compounds applicable in new generation herbicides, in an attempt to employ similar compounds to those produced naturally in ecosystems that provoke effective herbicide effects at low concentrations.

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Synthesis of 7-Oxo-5-deoxystrigol, a 7-Oxygenated Strigolactone Analog

Abstract: A straightforward synthesis of 7-oxo-5-deoxystrigol, a 7-oxygenated strigolactone analog, was achieved by starting from 2,2-dimethylcyclohexane-1,3-dione.

Cited by 7 publications

References 14 publications

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

Bioconversion of 5-deoxystrigol stereoisomers to monohydroxylated strigolactones by plants

Synthesis of strigolactones, a strategic account

Strategies for the synthesis of canonical, non-canonical and analogues of strigolactones, and evaluation of their parasitic weed germination activity

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