Total Synthesis of Sperabillin A and C

The first total synthesis of sperabillin A and an improved total synthesis of sperabillin C have been achieved in 11 steps from N-Boc-O-methyl-L-tyrosine. The stereoselective pathway to the core (3R,5R)-3,6-diamino-5-hydroxyhexanoic acid involves an Arndt-Eistert homologation, an asymmetric Henry reaction and a ruthenium tetroxide-catalyzed oxidative degradation of a benzene ring as key steps.