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Protecting Group-Free Total Synthesis of (-)-Boscartin H.

Hiroto AiharaDaisuke KounaiAkihiko KasamatsuJunya ShiraiwaAkinobu MatsuzawaShogo KamoKazuyuki Sugita
Published in: The Journal of organic chemistry (2024)
Herein, we report the first protecting group-free total synthesis of (-)-boscartin H, which features a 5-12-5-fused tricyclic structure. The key steps, which include a diastereoselective THF-ring-forming/aldol reaction sequence and ring-closing metathesis, afforded high stereoselectivity with (-)-boscartin H obtained in 3.6% overall yield using a 11-step long linear sequence. In addition, X-ray crystallography clearly confirmed the stereochemistry of boscartin H.
Keyphrases
  • high resolution
  • amino acid
  • magnetic resonance imaging
  • neural network