187328-75-2

Upstream product

• 623-36-9 (E)-2-methylpent-2-enal 
• 77877-20-4 (4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one 

Downstream Products

• 16251-45-9 (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one 
• 187328-76-3 (E)-(2R,3S)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide 

Relevant academic research and scientific papers

Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: Isolation, structure determination, synthesis, and biological activity

The bioassay-guided fractionation of the cytotoxic constituents of the Japanese sea hare Dollabella auricularia led to the isolation of aurilide (1), a 26-membered cyclodepsipeptide. The gross structure of 1 was established by spectroscopic analysis including 2D NMR techniques. The absolute stereostructure was determined by chiral HPLC analysis of acid hydrolysates of 1 and by the enantioselective synthesis of a degradation product arising from a dihydroxylated fatty acid portion. The enantioselective synthesis of 1 was achieved in 12% overall yield (16 steps) and confirmed the absolute stereostructure of 1. The cytotoxicity of 1 was evaluated using a synthetic sample, which was found to exhibit potent cytotoxicity against HeLa S 3 cells with an IC50 of 0.011 μg/mL. Further biological and pharmacological studies of 1 have been carried out by using synthetic 1. Graphical abstract.

Enantioselective Synthesis of Aurilide, a Cytotoxic 26-Membered Cyclodepsipeptide of Marine Origin

Aurilide (1), a novel cyclodepsipeptide isolated from the Japanese sea hare Dolabella auricularia, was enantioselectively synthesized, and the present result unambiguously confirmed its stereostructure. In addition, the cytotoxicity of 1 was evaluated by