Hydantocidin and Cornexistin

Takahashi, Shuji; Nakajima, Mutsuo; Kinoshita, Takeshi; Haruyama, Hideyuki; Sugai, Soji; Honma, Toyokuni; Sato, Sadao; Haneishi, Tatsuo

doi:10.1021/bk-1994-0551.ch006

Cited by 12 publications

(13 citation statements)

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“…Cornexistin ( Figure 2) is a patented herbicide extracted from the saprophytic basidiomycete Paecilomyces variotii (58,59). It is active against dicotyledonous weeds and some monocotyledonous weeds.…”

Section: Phytotoxins From Microbesmentioning

confidence: 99%

“…Hydantocidin ( Figure 2) is a relatively new patented herbicide from Streptomyces hygroscopicus (59,61,62). Hydantocidin is highly effective as a herbicide against both monocotyledonous and dicotyledonous weeds.…”

Section: Phytotoxins From Microbesmentioning

confidence: 99%

“…Hydantocidin is highly effective as a herbicide against both monocotyledonous and dicotyledonous weeds. Its low fermentation yield has resulted in development of synthetic procedures that give good yields (59,(62)(63)(64). It is non-selective and, thus, could only be used selectively with crops if the crops can be genetically engineered to be resistant, as been done with other non-selective herbicides (21).…”

Section: Phytotoxins From Microbesmentioning

confidence: 99%

“…For example, the commercial herbicide methoxyphenone was the result of QSAR studies with anisomycin (82,83). Nevertheless, the search for simpler active analogs that might be economically synthesized has been unsuccessful for tentoxin (57), hydantocidin (59), and many other natural phytotoxins.…”

Section: Development Factorsmentioning

confidence: 99%

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Natural Products with Potential Use as Herbicides

Duke

Abbas

1994

ACS Symposium Series

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There is great incentive to discover effective and economically feasible herbicides that are toxicologically and environmentally benign.Several hundred active ingredients of herbicides are now sold world-wide. Virtually all of these compounds were discovered by screening compounds from organic chemical synthesis programs.Leads for the structure of one group of patented herbicides came from 1,8-cineole, a well known plant allelochemical. However, plants have thus far not been as lucrative as microbial products as a source of phytotoxic compounds with the potential for direct use as herbicides or as templates for new synthetic herbicide classes. Microbial phytotoxins have provided valuable information on potential molecular target sites for herbicides. This information has also been useful in probing the biochemistry of plants. Phosphinothricin (glufosinate when synthetic), a product of Streptomyces viridochromogenes, is a successful herbicide that is environmentally and toxicologically benign. Bialaphos, a tripeptide from S. hygroscopicus which degrades to phosphinothricin in target plants, is the only commercial herbicide produced by biosynthesis. Many other microbial products have been patented as herbicides and some of these are under active development.Most of these compounds are from non-plant pathogens; however, there is growing interest in utilizing plant pathogens as sources of herbicide leads. Tentoxin, cornexistin, and AAL-toxin are discussed in detail as examples of microbial toxins with the potential for herbicide development. An overview of natural phytotoxins that have been considered for herbicides is provided, as well as considerations of the pesticide industry in using this approach. This chapter not subject to U.S.

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Section: Phytotoxins From Microbesmentioning

confidence: 99%

Section: Phytotoxins From Microbesmentioning

confidence: 99%

Section: Phytotoxins From Microbesmentioning

confidence: 99%

Section: Development Factorsmentioning

confidence: 99%

See 2 more Smart Citations

Natural Products with Potential Use as Herbicides

Duke

Abbas

1994

ACS Symposium Series

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“…[7] The observed activities were within the range of commercially available herbicides like bialaphos or glyphosate. These findings, paired with the low toxicity against mammals, plants and fungi[ 1a , 1b , 1c ] have drawn considerable interest from agrochemists to explore the cornexistins as lead compounds for the development of new broad‐spectrum herbicides. Herein, we report a full account of the development of a synthetic strategy that enabled us to accomplish the first total synthesis of (+)‐cornexistin ( 1 ).…”

Section: Introductionmentioning

confidence: 99%

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin

Wildermuth

Steinborn

Barber

et al. 2021

Chemistry A European J

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Herein is given a full account of the evolution of the first total synthesis of (+)‐cornexistin. Initial efforts were based on masking the reactive maleic anhydride moiety as a 3,4‐substituted furan and on forming the nine‐membered carbocycle in an intramolecular Conia‐ene or Nozaki–Hiyama–Kishi (NHK) reaction. Those strategies suffered from low yields and were jeopardized by a late‐stage installation of the Z‐alkene, as well as the stereocenters along the eastern periphery. These issues were addressed by employing a chiral‐pool strategy that involved construction of the crucial stereocenters at C2, C3 and C8 at an early stage with installation of the maleic anhydride as late as possible. The successful approach featured an intermolecular NHK coupling to install the Z‐alkene, a syn‐Evans‐aldol reaction to forge the stereocenters along the eastern periphery, an intramolecular allylic alkylation to close the nine‐membered carbocycle, and a challenging stepwise hydrolysis of a β‐keto nitrile to furnish the maleic anhydride.

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(+)‐Hydantocidin

2005

Synthesis of Naturally Occurring Nitrogen Heterocycles From Carbohydrates

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Hydantocidin and Cornexistin

Cited by 12 publications

References 0 publications

Natural Products with Potential Use as Herbicides

Natural Products with Potential Use as Herbicides

Evolution of a Strategy for the Total Synthesis of (+)‐Cornexistin

(+)‐Hydantocidin

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