Total synthesis of (+)-4-deoxygigantecin

Article abstract of DOI:10.1016/S0040-4020(98)00285-3

A total synthesis of a non-adjacent bis-tetrahydrofuranyl annonaceous acetogenin, (+)-4-deoxygigantecin (1) is described. Mono-tetrahydrofuran building block (10), of which the synthesis from (-)-muricatacin (8) had been described in an earlier report, was converted to bis-MOM ether (9) through two-step reactions. Transformation of this compound into non-adjacent bis- tetrahydrofuran unit (5) was carried out by a twelve-step sequence of reactions. Pd(0)-catalyzed cross coupling reaction between 5 and iodinated butenolide (7), which had been prepared from (S)-(-)-ethyl lactate, led to enyne (4). Finally, this compound was converted to (+)-4-deoxygigantecin (1) by two steps.