29428-96-4Relevant academic research and scientific papers
Synthesis of the Proposed Isomers of the Deep-Sea Mussel Metabolites Bathymodiolamides A and B
B?r, Alexander,B?r, Sofia I.,R?der, Moritz,Schobert, Rainer
, p. 1868 - 1873 (2021)
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.
