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

Karnjit ParmarPouyan HaghshenasMichel Gravel
Published in: Organic letters (2021)
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.
Keyphrases
  • electron transfer
  • ionic liquid