Total Synthesis of (+)-Neomarinone

The first total synthesis of (+)-neomarinone has been achieved by following a concise and convergent route using methyl (R)-lactate and (R)-3-methylcyclohexanone as chiral building blocks. Key steps of the synthesis are the stereo-controlled formation of the two quaternary stereocenters by diastereoselective 1,4-conjugate addition and enolale alkylation reactions. and the construction of the furanonaphthoquinone skeleton by rcgioselective Diels-Alder reaction between a 1,3-bis(trimethylsilyloxy)-1,3-diene and a bromoquinone. The synthesis proves the relative and absolute stereochemistry of natural neomarinone.