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  • Title: Total synthesis of (+)-neomarinone.
    Author: Peña-López M, Martínez MM, Sarandeses LA, Pérez Sestelo J.
    Journal: Chemistry; 2009; 15(4):910-6. PubMed ID: 19053110.
    Abstract:
    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.
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