Asymmetric synthesis of the C1–C6 portion of the psymberin using an Evans chiral auxiliary

The C1–C6 region of the potent cytotoxic agent psymberin has been synthesized. The key transformations of the synthesis are an auxiliary-controlled addition of a Sn(II)-glycolate enolate to an aldehyde to yield the anti-aldol product and transforming the primary alcohol into a terminal olefin utilizing organoselenium chemistry.