Studies in marine macrolide synthesis: Stereocontrolled synthesis of the C1-C11 and C15-C27 subunits of aplyronine A

Article abstract of DOI:10.1016/S0040-4039(98)01191-5

The aplyronine C₁-C₁₁ subunit 4, containing 4 stereocentres and the (E,E)-diene system, was prepared in 7 steps from ethyl ketone (R)-8 using a boron-mediated anti aldol reaction. The corresponding C₁₅-C₂₇ subunit 5, containing 6 stereogenic centres and an (E)-alkene, was obtained in 10 steps from ketone (S)-14 using a tin(II)-mediated syn aldol reaction and CBS enone reduction.