An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence

An efficient synthesis of the C1–C14 subunit resident in (−)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander–Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented β-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain.