Die Konstitution von Epoxydon

Abstract

Die Gattung P h w a gehiirt zur IClasse der Fungi Imperfecti, Familie Sphaerioiduceae, und ist bisher erst in wenigen Fallen chernisch untersucht worden. F

Synthesis of (±)-Epoxydon and Related Natural Compounds

“…Phyllostine (1) and epoxydon (2) are phytotoxic metabolites isolated from the culture filtrate of Phyllosticta sp, a pathogenic fungus of red clover, as the principal toxic compounds causing wilting and simultaneous dark discoloration of leafy stem cuttings of the host plant.l) Epoxydon was also isolated from Phoma sp. as a cytotoxic compound.…”

“…as a cytotoxic compound. 2 ) Epiepoxydon (3) was initially obtained as a synthetic artifact 3 ) together with epoxydon, and later characterized as a phytotoxin along with epiepoformin (5) from an unidentified fungus, separated from diseased leaves of crapemyrtle (Lagerstroemia indica L.), 4) and then identified as an intermediate in the patulin pathway in Penicillium urticae. 5 ) Epoformin (4) is an antibiotic and cytotoxic compound.…”

Synthesis ofdl-Phyllostine anddl-Epoxydon (Phyllosinol)

“…which causes marked darkening on the foliage of red clover,!) Among them two phytotoxins, phyllostine (1) and phyllosinol (2) were chemically correlated each other 1bJ and further it was confirmed that phyllosinol is identical with epoxydon which was isolated from phoma sp. .as an antitumor substance.…”

Synthesis of dl-Phyllostine and dl-Epoxydon (Phyllosinol)

“…which causes marked darkening on the foliage of red clo ver.1) Among them two phytotoxins, phyl lostine (1) and phyllosinol (2) were chemically correlated each other1b) and further it was confirmed that phyllosinol is identical with epoxydon which was isolated from phoma sp. as an antitumor substance.2) Epoxydon has, beside antitumor activity, broad physiological activities, such as stimulation of root elonga tion and antibiotic activity.3) In the present paper, we describe the first synthesis of these two compounds4,5) from 2-hydroxymethyl-1,4-benzoquinone (3).…”