Synthesis of C1-C10 fragment of Muamvatin.

: This report delineates our efforts towards the synthesis of a stereochemically well-defined ketone,  C 1 -C 10  fragment of muamvatin, the first example of 2, 4, 6-trioxaadamantane ring skeletal polypropionate marine natural product, using two non-aldol variants. i) 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 protocal, a NHC-mediated reaction on  β -epoxy aldehydes, was utilized for stereoselective construction of methyl and hydroxyl groups in  anti -fashion .