4.8 Article

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

Journal

ORGANIC LETTERS
Volume 23, Issue 4, Pages 1416-1421

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00090

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Funding

  1. Natural Sciences and Engineering Research Council (NSERC) of Canada [RGPIN-2017-06230]
  2. Canada Foundation for Innovation
  3. University of Saskatchewan
  4. Saskatchewan Structural Sciences Centre (SSSC)

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This study presents the shortest synthesis of the glycosidase inhibitor (+)-hyacinthacine A(1) using a highly chemoselective N-heterocyclic carbene-catalyzed crossbenzoin reaction and a furan photooxygenation-amine cyclization strategy. The unprecedented cyclization on a furylic alcohol due to the instability of formed intermediates was successfully achieved, eventually leading to the formation of the requisite pyrrolizidine framework through a three-step one-pot process.
We report the shortest synthesis of glycosidase inhibitor (+)-hyacinthacine A(1) using a highly chemoselective N-heterocyclic carbene-catalyzed crossbenzoin 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 A(1).

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