A new synthesis of (−)-epipyriculol: a phytotoxic metabolite

Leyva, Antonio; Blum, Francesca E.; Ley, Steven V.

doi:10.1016/j.tet.2008.01.115

Cited by 13 publications

(8 citation statements)

References 35 publications

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“…In fact, the ESIMS spectrum of 3 showed the potassium [M + K] + and sodium [M + Na] + adduct ions at m/z 287 and 271. The optical rotation ([α] D 25 = −31.2 ( c = 0.7 CHCl 3 ) was very similar to that reported in the literature for the natural and synthetic (10 S )‐isomer of pyriculol, named epipyriculol. The ESIMS spectrum of 4 showed the sodium [M + Na] + adduct ion and the protonated form [M + H] + at m/z 217 and 195, respectively.…”

Section: Resultssupporting

confidence: 82%

“…[α] 25 D –31.2 ( c 0.07 in CHCl 3 ) [lit. 26 : [α] 25 D –31 ( c 0.41 in CHCl 3 )]; 1 H NMR spectrum was very similar to that previously described ; ESIMS ( m/z ): 287 [ M + K] + , 271 [ M + Na] + .…”

Section: Methodssupporting

confidence: 62%

“…P. grisea was produced in liquid culture and the organic extract obtained from the culture filtrates was purified as reported in detail in the Experimental section; five metabolites were isolated. Three of these compounds were identified, by comparing their spectroscopic (IR, UV, and 1 H NMR spectra) data with those previously reported in the literature, as (10 S ,11 S )‐(−)‐epipyriculol, trans ‐3,4‐dihydro‐3,4,8‐trihydroxy‐1(2 H )‐napthalenone and (4 S )‐isosclerone ( 3 , 4, and 5 , respectively, Figure ) . Their identification was confirmed by the ESIMS spectra and physical (optical rotation) data.…”

Section: Resultsmentioning

confidence: 54%

“…This article reports on the isolation and chemical and biological characterization of two monosubstituted hex‐4‐ene‐2,3‐diols, named pyriculins A and B ( 1 and 2 ; Figure ) together with (10 S ,11 S )‐(−)‐epipyriculol, trans ‐3,4‐dihydro‐3,4,8‐trihydroxy‐1(2 H )‐napthalenone, and (4 S )‐(+)‐isosclerone ( 3 , 4, and 5 , respectively; Figure ).…”

mentioning

confidence: 99%

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Pyriculins A and B, two monosubstituted hex‐4‐ene‐2,3‐diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)

et al. 2017

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Pyricularia grisea has been identified as a foliar pathogen on buffelgrass (Cenchrus ciliaris) in North America and was studied as a potential source of phytotoxins for buffelgrass control. Two monosubstituted hex-4-ene-2,3-diols, named pyriculins A and B, were isolated from its culture filtrate organic extract together with (10S,11S)-(-)-epipyriculol, trans-3,4-dihydro-3,4,8-trihydroxy-1(2H)-napthalenone, and (4S)-(+)-isosclerone. Pyriculins A and B were characterized by spectroscopic (essentially nuclear magnetic resonance [NMR], High-resolution electrospray ionization mass spectrometry [HRESIMS]) and chemical methods such as (4E)-1-(4-hydroxy-1,3-dihydroisobenzofuran-1-yl)hex-4-ene-2,3-diols. The relative and absolute configuration of these compounds was determined by a combination of spectroscopic (NMR, electronic circular dichroism [ECD]) and computational tools. When bioassayed in a buffelgrass coleoptile and radicle elongation test, (10S,11S)-(-)-epipyriculol proved to be the most toxic compound. Seed germination was much reduced and slowed with respect to the control and radicles failed to elongate. All five compounds delayed germination, but only (10S,11S)-(-)-epipyriculol was able to prevent radicle development of buffelgrass seedlings. It had no effect on coleoptile elongation, while the other four compounds caused significantly increased coleoptile development relative to the control.

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Section: Resultssupporting

confidence: 82%

Section: Methodssupporting

confidence: 62%

Section: Resultsmentioning

confidence: 54%

mentioning

confidence: 99%

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Pyriculins A and B, two monosubstituted hex‐4‐ene‐2,3‐diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)

et al. 2017

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“…Thus, examining their secondary metabolism leads to the discovery of novel compounds with interesting structures or modes of action that could be useful for agrochemistry or pharmacology [5]. In the work, chemical investigations of a strain M. grisea M639 have led to the discovery of four new aromatic polyketides griseaketides A-D (1-4), as well as 15 known compounds (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). Herein, we describe the isolation, structural elucidation and nematicidal activities of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Griseaketides A–D, New Aromatic Polyketides from the Pathogenic Fungus Magnaporthe grisea

Yang

Lei

et al. 2019

Molecules

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Magnaporthe grisea is the causal agent of rice blast disease, which is the most serious disease of cultivated rice. Aromatic polyketides are its typical metabolites and are involved in the infection process. In the search for novel lead compounds, chemical investigation of the fungus M. grisea M639 has led to the isolation of four new aromatic polyketides (salicylaldehyde skeleton bearing an unsaturated side chain), griseaketides A–D (1–4), as well as 15 known compounds (5–19). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses, including HR-MS, 2D NMR. Compound 12 showed prominent activity that killed 94.5% of C. elegans at 400 ppm and 66.9% at 200 ppm over 24 h. This is the first report describing the nematicidal activity of this type aromatic polyketide.

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TheJulia–Kocienski Olefination

Blakemore¹,

Sephton

Ciganek

2018

Organic Reactions

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The Julia–Kocienski olefination is a direct connective synthesis of alkenes via the addition of metalated aryl alkyl sulfones to carbonyl compounds. The activating aromatic group associated with the sulfone must possess electrophilic character, and alkene formation occurs via β‐alkoxy sulfone formation, transfer of the aryl group from sulfur to oxygen via a Smiles rearrangement, and then elimination of sulfur dioxide and an aryloxide anion from the resulting β‐aryloxy sulfinate anion. The olefination process itself and the methods used to prepare the requisite sulfone substrates are tolerant of a wide variety of functional groups, and a variety of alkene targets can be prepared. Stereoselectivity is dependent on the nature of the sulfone, the carbonyl compound, the activating aryl moiety, and the reaction conditions. This chapter describes theoretical and operational aspects of the Julia–Kocienski olefination such that the reader will be able to obtain optimal results in his/her own research. A detailed mechanistic overview is included to account for the factors that influence stereoselectivity and yield. Methods for introducing sulfone activators into fragments of interest, best practices for generating sulfone anions, and optimal strategies for targeting different classes of alkene targets are discussed. Functional group compatibilities, reaction variants, and a comparison to other methods of alkene synthesis are also presented. Tabular surveys are organized according to type of alkene synthesized, with an emphasis on the degree of substitution and the level of conjugation about the newly formed double bond. The literature is covered from the initial disclosure of the Julia–Kocienski olefination in 1991 to the first quarter of 2016.

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A new synthesis of (−)-epipyriculol: a phytotoxic metabolite

Cited by 13 publications

References 35 publications

Pyriculins A and B, two monosubstituted hex‐4‐ene‐2,3‐diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)

Pyriculins A and B, two monosubstituted hex‐4‐ene‐2,3‐diols and other phytotoxic metabolites produced by Pyricularia grisea isolated from buffelgrass (Cenchrus ciliaris)

Griseaketides A–D, New Aromatic Polyketides from the Pathogenic Fungus Magnaporthe grisea

TheJulia–Kocienski Olefination

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