A Concise Enantioselective Total Synthesis of (−)-Deoxoapodine

Kei Yoshida, Kosuke Okada, Hirofumi Ueda, Hidetoshi Tokuyama

研究成果: Article査読

3 被引用数 (Scopus)

抄録

We have established a highly convergent 10-step route for the total synthesis of (−)-deoxoapodine, which is a hexacyclic aspidosperma alkaloid. The quaternary C5 center of the characteristic tetrahydrofuran ring was constructed by a chiral-phosphoric-acid-catalyzed enantioselective bromocycloetherification in a 5-endo fashion and subsequent allylation by using the Keck protocol. Construction of the aspidosperma skeleton features the formation of a nine-membered lactam by a catalytic C−H palladation/alkylation cascade at the indole 2-position and an iron-catalyzed oxidative transannular reaction at a late-stage of the synthesis.

本文言語English
ページ(範囲)23089-23093
ページ数5
ジャーナルAngewandte Chemie - International Edition
59
51
DOI
出版ステータスPublished - 2020 12 14

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)

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