Synthetic studies toward the microtubule-stabilizing agent laulimalide: synthesis of the C1–C14 fragment

The C1–C14 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 15 steps from l-(−)-citronellal. The C9 chiral center was established using an asymmetric allylation, the dihydropyran ring was prepared through ring-closing metathesis, and the exo-methylene was incorporated using Eschenmoserʹs salt.