A Concise Enantioselective Total Synthesis of (−)-Deoxoapodine

Kei Yoshida, Kosuke Okada, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)23089-23093
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number51
DOIs
Publication statusPublished - 2020 Dec 14

Keywords

  • C−H functionalization
  • alkaloids
  • haloetherification
  • oxidation
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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