Catalytic asymmetric formal synthesis of beraprost

• 竹本, 佳司

• Kuramoto, Ryuta

• Takemoto, Yoshiji

抄録

The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α, β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C-C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C-H insertion and the subsequent reduction from the convex face.

収録刊行物

• Beilstein Journal of Organic Chemistry

  Beilstein Journal of Organic Chemistry 11 2654-2660, 2015-12-18

  Beilstein-Institut

キーワード

• Bifunctional catalysis
• Hydrogen bonding
• Organocatalyst
• Oxa-Michael
• Prostacyclin

詳細情報

• CRID: 1050845760773807488
• NII論文ID: 120006027170
• ISSN: 18605397
• HANDLE: 2433/219534
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles