Synthesis of the Proposed Isomers of the Deep-Sea Mussel Metabolites Bathymodiolamides A and B

J Org Chem. 2021 Jan 15;86(2):1868-1873. doi: 10.1021/acs.joc.0c02726. Epub 2021 Jan 4.

Abstract

The first total synthesis of bathymodiolamides A and B, ceramide-like metabolites of the deep-sea hydrothermal vent mussel Bathymodiolus thermophilus, was accomplished in eight linear steps starting from Garner's aldehyde and three carboxylic acids. A sequence of vinylation of Garner's aldehyde, N-acylation with lauric acid, dihydroxylation of the terminal alkene, and stepwise Steglich-Hassner esterifications of the resulting vicinal diol with the respective saturated and unsaturated carboxylic acids, which had to be prepared separately, afforded the target products in 38 and 39% yield. We found distinct discrepancies between their NMR data and antiproliferative activities and those reported for the natural isolates.

MeSH terms

  • Animals
  • Ceramides
  • Hydrothermal Vents*
  • Isomerism
  • Mytilidae*

Substances

  • Ceramides