Total synthesis of (+)-neomarinone.

Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.


Chem. Eur. J. 2009, 15, 910–916 (DOI: 10.1002/chem.200802021).

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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 stereocontrolled formation of the two quaternary stereocenters by diastereoselective 1,4-conjugate addition and enolate alkylation reactions, and the construction of the furanonaphthoquinone skeleton by regioselective 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.