Total Syntheses of the Structures Assigned to Denigrins A, B, C, F, and G, 3,4-Diaryl-Pyrrole and -Pyrrolidinone Alkaloids, and the Conversion of Congener B into the Co-metabolite Spirodactylone

J Nat Prod. 2024 Jun 28;87(6):1521-1531. doi: 10.1021/acs.jnatprod.3c01177. Epub 2024 May 16.

Abstract

The title marine natural products have been prepared by total synthesis and in the case of congeners 3, 6, and 7 for the first time. Each of these was obtained by manipulation of readily prepared denigrin B (2). The structure, 3, assigned to denigrin C is shown to be incorrect. Reaction of compound 2 with DDQ has led, in high yield, to the related natural product spirodactylone (16), while treating the corresponding permethyl ether 15 with PIFA/BF3·Et2O provides compound 20, embodying an isomeric framework.

MeSH terms

  • Alkaloids* / chemical synthesis
  • Alkaloids* / chemistry
  • Animals
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Marine Biology
  • Molecular Structure
  • Pyrroles* / chemical synthesis
  • Pyrroles* / chemistry
  • Pyrrolidinones* / chemical synthesis
  • Pyrrolidinones* / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Pyrroles
  • Pyrrolidinones
  • Biological Products