NEW BIOACTIVE TRITERPENOIDS AND SECO-TRITERPENOIDS.

摘要

The new triterpenoids of general formulae (I), (II), (III) and (IV) where R<1> represents a dialkyl, trialkyl, triphenyl, diphenylalkyl, alkyldiphenyl, dialkylphenyl, haloalkyl, halophenylalkyl, allylalkyl or alkylaminoalkyl group and R<2> represents a carboxyl group, salt or ester, and a process for their preparation which comprises reaction of friedelin with a silylating agent in the presence of a bulky strong base, with kinetic or thermodynamic control, to produce regio-specifically compounds of general formula (I) or (II). Oxidation of (I) or (II) yields the corresponding hydroxy ketones (VII) or (VIII), from which acyl and glycosyl derivatives can be prepared, and further oxidation of the hydroxy ketones (VII) or (VIII) with peracid gives the seco-aldehyde acids (III) or (IV), from which esters or salts can be prepared. Ozonolysis of (I) or (II), followed by reductive treatment, produces the diols of formula (IX) or (X), from which acyl and glycosyl derivatives can be prepared. Oxidation of (I) with a benzoquinone leads to friedel-1-en-2-one (XI) in high yields. Compounds or combinations of compounds (I), (II), (III), (IV), (VI), (VII), (VIII), (IX), (X), (XII), including the acyl and glycosyl derivatives thereof, find application in fungicidal, bactericidal, antitumour and antifeedant compositions.