Synthetic studies on annonaceous acetogenins .5. Syntheses of two possible diastereoisomers of the epoxy lactone proposed for an annonaceous acetogenin, epoxyrollin A

Syntheses of two possible diastereoisomers (5S, 18'S, 19'R)- and (5S, 18'R, 19'S)-1 corresponding to the epoxy lactone that has been proposed for epoxyrollin A, a structural representative of biosynthetic precursors of tetrahydrofuran annonaceous acetogenins, are described. The C-13-NMR and tandem mass spectral data of the synthetic samples were not in accord with those recorded for natural epoxyrollin A. Consequently, the structure of epoxyrollin A needs to be revised. Copyright (C) 1996 Elsevier Science Ltd