Reticulatain-1 and -2 with reticulatamone: three new polyketides from the seeds of annona reticulata [1]

We have isolated four annonaceous acetogenins of identical molecular formula C 37 II 68 O 5 from Annona reticulata seeds. They all belong to the A1 type (one tetrahydrofuran ring). Two of them, reticulatain-1 and reticulatain-2, are new and possess the very rare threo-trans-erythro stereochemical relationship across the THF ring. The other two, reticulatacin and uvariamicin III, were also isolated and fully characterized since uvariamicin III was only reported as a component of a mixture. Furthermore, a new acetogenin precursor was extracted and characterized, possessing a single asymmetric center of (S) absolute configuration, as proved by its total synthesis.