The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone

J Am Chem Soc. 2006 Jun 21;128(24):7738-9. doi: 10.1021/ja061853f.

Abstract

Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / pharmacology
  • Catalysis
  • Diterpenes / chemical synthesis*
  • Diterpenes / pharmacology
  • Models, Chemical
  • Palladium / chemistry
  • Salvia miltiorrhiza / chemistry*
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes
  • dichroanone
  • Palladium