The total synthesis of (2S,3S)-2,3-dihydro-6-[(1‘S, 2‘R)-2-hydroxy-1-methylbutyl]-3,5-dimethyl-2-[(1‘ ‘S)-1-methylpropyl]-4H-pyran-4-one (3), the (−)enantiomer of the marine polypropionate, maurenone, was achieved in nine linear steps (13% overall yield) from (R)-2-benzylpentan-3-one ((R)-14) and (R)-2-benzoyloxypentan-3-one ((R)-15). Key fragments were synthesized using highly diastereoselective syn and anti boron aldol reactions and were coupled using a lithium-mediated aldol reaction. Trifluoroacetic acid-promoted cyclization/dehydration was then used to install the γ-dihydropyrone ring. Eight isomers of one enantiomeric series were synthesized by coupling two ketones with each of four aldehydes. Comparison of the ¹³C NMR data for the eight isomers with that reported for maurenone established the relative stereochemistry of the natural product.