Total Synthesis of (+)-Hyacinthacine A1 Using a Chemoselective Cross-Benzoin Reaction and a Furan Photooxygenation-Amine Cyclization Strategy

Org Lett. 2021 Feb 19;23(4):1416-1421. doi: 10.1021/acs.orglett.1c00090. Epub 2021 Feb 4.

Abstract

We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A1 using a highly chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reaction as well as a furan photooxygenation-amine cyclization strategy. This is the first such cyclization on a furylic alcohol, an unprecedented reaction due to the notorious instability of the formed intermediates. The photooxygenation strategy was eventually incorporated into a three-step one-pot process that formed the requisite pyrrolizidine framework of (+)-hyacinthacine A1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Benzoin / chemistry*
  • Catalysis
  • Cyclization
  • Furans / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amines
  • Furans
  • carbene
  • Benzoin
  • Methane