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 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.
Peña-López
Miguel
M
Departamento de Química Fundamental, Universidade da Coruña, Campus Zapateira, s/n; 15071A Coruña, Spain.
Martínez
M Montserrat
MM
Sarandeses
Luis A
LA
Pérez Sestelo
José
J
D000478:Alkylation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009285:Naphthoquinones; C493875:neomarinone