Synthetic studies toward the microtubule-stabilizing agent laulimalide: synthesis of the C 15–C 28 fragment

Abstract

The C 15–C 28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps with an overall yield of 14%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry and the 19,20- syn-diol was generated through the addition of a mixed vinyl zincate to a protected α-hydroxyaldehyde.