Total Synthesis of (-)-Lepadiformine A via Radical Translocation-Cyclization Reaction

Masashi Shimomura, Manabu Sato, Hiroki Azuma, Juri Sakata, Hidetoshi Tokuyama

研究成果: Article査読

4 被引用数 (Scopus)

抄録

Total synthesis of (-)-lepadiformine A featuring construction of the 1-azaspiro[4.5]decane skeleton by a highly diastereoselective radical translocation-cyclization reaction of a γ-lactam derivative bearing a chiral butenolide moiety is described. The enantioselective construction of butenolide is conducted via Krische's catalytic asymmetric allylation protocol. After the radical translocation-cyclization reaction, a hydroxymethyl group at the C-13 position was stereoselectively introduced by a one-pot partial reduction-allylation protocol of the unprotected lactam derivative. Finally, the total synthesis is completed by formation of a C ring.

本文言語English
ページ(範囲)3313-3317
ページ数5
ジャーナルOrganic letters
22
9
DOI
出版ステータスPublished - 2020 5月 1

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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