The total synthesis of (+)-iriciniastatin A (psymberin) is reported in 19 steps and 6% overall yield. Key reactions include a highly convergent enolsilane-oxocarbenium ion union to generate the C8-C25 fragment and a late-stage coupling of a hemiaminal and acid chloride to complete the synthesis.
A convenient method to introduce a sulfone group to pyridines and diazines is described. This efficient method involves the conjugate addition of sodium methanesulfinate to vinyl heterocycles. This process tolerates a wide variety of functional groups and is performed in the presence of acetic or trifluoroacetic acid. A one-pot, two-step synthesis of sulfones starting from the corresponding heteroaryl halide is also described.