Total Synthesis of Tanshinone I

J Nat Prod. 2017 May 26;80(5):1697-1700. doi: 10.1021/acs.jnatprod.7b00238. Epub 2017 Apr 26.

Abstract

A novel total synthesis of tanshinone I (1) via the intermediate 3-hydroxy-8-methyl-1,4-phenanthrenedione (8) is described. The low overall yields and the use of expensive reagents in the synthesis process were minimized by the use of the Diels-Alder reaction to directly construct the 1,4-phenanthrenedione scaffold, providing tanshinone I (1) in only three steps.

MeSH terms

  • Abietanes / chemical synthesis*
  • Abietanes / chemistry
  • Cycloaddition Reaction
  • Molecular Structure
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry

Substances

  • 3-hydroxy-8-methyl-1,4-phenanthrenedione
  • Abietanes
  • Phenanthrenes
  • tanshinone
  • 1,4-phenanthrenequinone