Skip to main content
eScholarship
Open Access Publications from the University of California

Total Synthesis of (-)-Chromodorolide B By a Computationally-Guided Radical Addition/Cyclization/Fragmentation Cascade.

  • Author(s): Tao, Daniel J
  • Slutskyy, Yuriy
  • Muuronen, Mikko
  • Le, Alexander
  • Kohler, Philipp
  • Overman, Larry E
  • et al.
Abstract

The first total synthesis of a chromodorolide marine diterpenoid is described. The core of the diterpenoid is constructed by a bimolecular radical addition/cyclization/fragmentation cascade that unites two complex fragments and forms two C-C bonds and four contiguous stereogenic centers of (-)-chromodorolide B in a single step. This coupling step is initiated by visible-light photocatalytic fragmentation of a redox-active ester, which can be accomplished in the presence of an iridium or a less-precious electron-rich dicyanobenzene photocatalyst, and employs equimolar amounts of the two addends. Computational studies guided the development of this central step of the synthesis and provide insight into the origin of the observed stereoselectivity.

Many UC-authored scholarly publications are freely available on this site because of the UC Academic Senate's Open Access Policy. Let us know how this access is important for you.

Main Content
Current View