CORIACYCLODIENIN AND CORIACYCLOENIN - 2 NEW ANNONACEOUS ACETOGENINS FROM ANNONA-CORIACEA

Two new Annonaceous acetogenins, coriacyclodienin (1) and coriacycloen in (2), have been isolated from the roots of Annona coriacea Mart. (An nonaceae). 1 is the first mono-THF acetogenin which bears two double b onds in the aliphatic chain, while 2 has the same mono-THF ring and on ly one double bond. Both compounds (1) and (2) were oxidized and cycli zed, in a one pot reaction, to give the mixtures of the four possible stereoisomer derivatives (3, 4, 5 and 6) of 1 and the two possible ste reoisomer derivatives (7 and 8) of 2. The absolute stereochemistries o f 1 and 2 were assigned using NMR analysis of their Mosher esters and enzymatic method.