Synthesis of C-1-C-9 and C-10-C-21 Fragments of (-)-Dolabriferol

Our efforts on the synthesis of C-1-C-9 and C-10-C-21 subunits of dolabriferol, a non-contiguous polypropionate marine natural product, from a common intermediate using two non-aldol variants is reported. i) Shimizu reaction, a Pd(0) mediated stereoselective epoxy-ring opening of alkenyl oxiranes, has been employed for the stereoselective installation of methyl groups at C-4 and C-13 and ii) Bode's protocol, a NHC-mediated reaction on beta-epoxy aldehydes, has been utilized for stereoselective construction of methyl and hydroxyl groups in anti-fashion at C-6-C-7 and C-15-C-16 in the natural product.