Formal synthesis of schulzeines B and C: A new route to Gurjar's lactams

Chu-En Chou, Yi-An Chen, Yi-Ching Lin, Shih-Chieh Kao, Chieh-Yu Chang, Yen-Ku Wu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Described is a formal synthesis of racemic schulzeines B and C that intercepts intermediates developed by Gurjar and co-workers. The synthetic sequence features an annulative coupling of a ketimine and acrylic acid enabling the construction of the benzoquinolizidine nucleus in a highly convergent manner. We also examined a continuous-flow version of the thermal aza-annulation, which proved less practical as compared to the batch processes.

Original languageEnglish
Number of pages6
JournalJournal of the Chinese Chemical Society
DOIs
StateAccepted/In press - 20 Aug 2020

Keywords

  • 2-piperidone
  • aza-annulation
  • benzoqionolizidine
  • marine alkaloid
  • schulzeine
  • ALPHA-GLUCOSIDASE INHIBITORS
  • A-C
  • CORE
  • ACID

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