Synthesis and Configuration of O-Acetyl Microgrewiapine A: Phantomization of O-Acetyl 6- epi-Microgrewiapine A

J Nat Prod. 2022 Jan 28;85(1):306-312. doi: 10.1021/acs.jnatprod.1c00847. Epub 2021 Dec 17.

Abstract

The formation of O-acetyl microgrewiapine A is investigated. NMR data for the authentic sample derived from the natural product are corrected. Wholly synthetic samples, produced from reductive N-methylation of synthetic microcosamine A (to give synthetic microgrewiapine A) followed by O-acetylation, exhibit NMR data that are identical to those of the authentic sample. The previous report that this two-step transformation proceeds with epimerization at C-6 is thus shown to be in error: the purported sample of O-acetyl 6-epi-microgrewiapine A is structurally misassigned and is, in fact, O-acetyl microgrewiapine A. A plausible rationale for the structural misassignment is advanced.

MeSH terms

  • Acetylation
  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry*
  • Biological Products / chemistry
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Methylation
  • Molecular Structure
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Alkaloids
  • Biological Products
  • Piperidines
  • microgrewiapine A