63992-62-1Relevant academic research and scientific papers
Organochlorine compounds from a terrestrial higher plant: Structures and origin of chlorinated orcinol derivatives from diseased bulbs of Lilium maximowiczii
Monde, Kenji,Satoh, Hikari,Nakamura, Masao,Tamura, Mamoru,Takasugi, Mitsuo
, p. 913 - 921 (2007/10/03)
Seven chlorine-containing orcinol derivatives (2-8)and orcinol (9) have been isolated from diseased bulbs of the edible lily Lilium maximowiczii, and their structures have been elucidated. Six of the chlorinated orcinol derivatives (2, 4-8) showed antifungal activity. Because organochlorine compounds are rare in terrestrial higher plants, their biosynthetic origin was examined. These compounds were shown to be induced in intact bulb scales by UV irradiation or by inoculation with the pathogenic fungus Fusarium oxysporum f. sp. lilii. Biosynthetic studies suggested that these 'natural organochlorine pesticides' are produced by enzymatic chlorination of orcinol (9) with chloroperoxidase and hydrogen peroxide, which are both induced in the plant tissue under stress conditions.
The Synthesis and Ring-contraction of Halogenated Hydroxyquinones; a New Synthesis of Cryptosporiopsin
Henderson, Graeme B.,Hill, Robert A.
, p. 2595 - 2599 (2007/10/02)
Syntheses of 2,6-dichloro- and 2,6-dibromo-3-hydroxy-5-alkyl-1,4-benzoquinones have been developed involving oxidation of trihalogenoresorcinol derivatives with Fremy's salt.The reactions of these quinones have been studied and their ring-contraction to cyclopentenoid structures on treatment with N-halogenosuccinimides is reported.This sequence of reactions has been used in an efficient synthesis of the fungal metabolite cryptosporiopsin.
