Synthesis of the C1 -C10 Fragment of Muamvatin.

This report delineates our efforts towards the synthesis of a stereochemically well-defined ketone, the C1 -C10 fragment of muamvatin, the first example of a 2, 4, 6-trioxaadamantane ring skeletal polypropionate marine natural product, using two non-aldol variants. i) The Shimizu reaction, a Pd(0) mediated stereoselective epoxy-ring opening of alkenyl oxiranes, was employed for the stereoselective installation of methyl groups in syn-fashion and ii) Bode's protocol, a NHC-mediated reaction on β-epoxy aldehydes, was utilized for stereoselective construction of methyl and hydroxyl groups in anti-fashion.