TOTAL SYNTHESIS OF SOLAMIN AND RETICULATACIN

A total synthesis of the natural products, solamin 1 and reticulatacin 2 is described. The monotetrahydrofuran moiety 12a of compounds 1 and 2 was constructed by an eight-step reaction sequence, starting from ( -)-muricatacin 5, an acetogenin derivative. The gamma-lactone moieties 26 and 27 of compounds 1 and 2 were prepared by a multi-stage procedu re, starting from (S)-(-)-ethyl lactate. A palladium-catalysed cross c oupling reaction of compound 12a with either compound 26 or compound 2 7 gave the products 28 and 29 which by a three-step sequence were conv erted into compounds 1 and 2 respectively. Similarly, 15,16-di-epi-sol amin 3 and 17,18-di-epi-reticulatacin 4 were synthesized.