1134565-75-5Relevant academic research and scientific papers
Total synthesis of (+)-neomarinone
Pena-Lopez, Miguel,Martinez, M. Montserrat,Sarandeses, Luis A.,Sestelo, Jose Perez
experimental part, p. 910 - 916 (2009/07/09)
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.
