Total Syntheses of the Structures Assigned to the Marine Natural Products Orthoscuticellines A-E

Liangguang Yi, Yu Tao He, Shen Tan, Lorenzo V. White, Ping Lan, Michael G. Gardiner, Zhipeng Pei, Michelle L. Coote, Martin G. Banwell

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)
55 Downloads (Pure)

Abstract

The readily prepared and vinylated β-carboline 11 has been converted over one or two steps into compounds 1-5, the structures assigned to the recently reported marine natural products orthoscuticellines A-E. The spectral data recorded on the synthetically derived compounds are fully consistent with the assigned structures and, on making allowances for variations in the pH of the medium in which the spectra of the natural products were recorded, it is concluded that the structures assigned to orthoscuticellines A-E are most likely correct. Certainly, the calculated 13C NMR spectra of the α-, γ-, and δ-carboline isomers of compounds 1-5 suggest that orthoscuticellines A-E do incorporate the assigned β-carboline core.

Original languageEnglish
Pages (from-to)12287–12296
Number of pages10
JournalJournal of Organic Chemistry
Volume87
Issue number18
Early online date29 Aug 2022
DOIs
Publication statusPublished - 16 Sept 2022

Keywords

  • Chemical structure
  • Hydrocarbons
  • Molecular structure
  • Nuclear magnetic resonance spectroscopy
  • Pharmaceuticals

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