51263-40-2Relevant articles and documents
Total Synthesis and Biological Evaluation of Zealactone 1a/b
Catak, Saron,Dakas, Pierre-Yves,De Mesmaeker, Alain,Dieckmann, Michael,Hermann, Katrin,Horoz, Beyza,Quinodoz, Pierre,Rendine, Stefano,Screpanti, Claudio,Yoshimura, Masahiko,Fonné-Pfister, Raymonde
, (2020)
Strigolactones are plant hormones, which play pivotal roles in plant growth and development with potential application in sustainable agriculture. Recently, zealactone 1a/b has been identified as the major strigolactone from the root exudates of corn. Although zealactone is a promising molecule affecting signaling in the rhizosphere as well as in planta, evaluating its biological activities has been hampered by its low natural abundance and its relative chemical instability. Herein, we present the total synthesis of zealactone 1a/b based on our studies employing a [2+2]-cycloaddition strategy and a chemoselective Baeyer-Villiger oxidation to forge the γ-butyrolactone fragment. Furthermore, we disclose the biological activities of zealactone 1a/b on corn and in soil in comparison with related synthetic analogues.
COMPOUNDS FOR INHIBITION OF FUNGAL MYCOTOXIN AND SPORULATION
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Paragraph 0149; 0150, (2018/07/30)
Compounds and compositions are described herein that inhibit the biosynthesis of mycotoxins and fungal sporulation. Such compounds and compositions are useful for inhibiting mold. Methods of using such compounds and compositions are also described herein that involve applying the compositions to plants, plant parts, structures, containers, and other surfaces.
Photosensitized oxygenation of twisted 1,3-dienes: Abnormally higher reactivity of vinyl hydrogen rather than allyl hydrogen toward singlet oxygen
Mori, Hajime,Ikoma, Keiichi,Isoe, Sachihiko,Kitaura, Kazuo,Katsumura, Shigeo
, p. 8704 - 8718 (2007/10/03)
As one of the novel examples to investigate the characteristic reactivity of significantly twisted 1,3-dienes, the photosensitized oxygenation of two types of significantly twisted 1,3-dienes, cis-βionol derivative 2 and acyclic derivative 11, is investigated. Photosensitized oxygenation of 2a-f and 11a-e revealed that the vinyl hydrogen Ha was more reactive than the allyl hydrogen Hb. Thus, phenyl derivative 2e and tert- butyl-substituted compound 11d selectively produced allenes 3e and 13d in 67% and 75% yield resulting from the ene reaction of the vinyl hydrogen Ha rather than allyl alcohols 4e and 14d resulting from the allyl hydrogen abstraction in 24% and 8% yield, respectively. Furthermore, in the case of methyl- substituted compound 11b, the extent of the inherent reactivity of the vinyl hydrogen Ha was similar to that of the allyl hydrogen Hc. On the basis of X- ray analysis and MM and MO calculations, the discovered abnormally higher reactivity of the vinyl hydrogen would be rationalized by considering mainly the large σ*-π orbital interaction between the vinyl C-H bond and another double bond in significantly twisted 1,3-dienes resulting from calculations of HOMO electron densities.
