Total synthesis of (±)-sacidumlignans D and A through Ueno-Stork radical cyclization reaction

Org Biomol Chem. 2013 Apr 21;11(15):2498-513. doi: 10.1039/c3ob00053b. Epub 2013 Feb 26.

Abstract

Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno-Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from analogous Ueno-Stork cyclization product 27 played an important role. Moreover, potentially biomimetic conversion from (±)-sacidumlignan D (4) to sacidumlignan A (1) could be realized.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Cyclization
  • Lignans / chemical synthesis*
  • Lignans / chemistry*
  • Models, Molecular
  • Molecular Conformation

Substances

  • Lignans
  • sacidumlignan A
  • sacidumlignan D