50464-58-9Relevant academic research and scientific papers
Total synthesis of (+)-neomarinone
Pena-Lopez, Miguel,Martinez, M. Montserrat,Sarandeses, Luis A.,Sestelo, Jose Perez
scheme or table, 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.
First stereoselective synthesis of (4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5- dimethyl-2(3H)-naphthalenone
Cuesta, Xavier,Gonzalez, Asensio,Bonjoch, Josep
, p. 3365 - 3370 (2007/10/03)
The synthesis of enantiomerically pure (4aS,5R)-hexahydro-4a,5-dimethyl- 2(3H)-naphthalenone (-)-1 is described for the first time. The synthesis starts from (R)-3-methylcyclohexanone and involves the preparation of Piers enol lactone 6 in its enantiopure
