Total synthesis of (+)-neomarinone

Chemistry. 2009;15(4):910-6. doi: 10.1002/chem.200802021.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry
  • Stereoisomerism

Substances

  • Naphthoquinones
  • neomarinone