219719-91-2

Upstream product

• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 219719-90-1 (S)-3-benzyloxy-1-dodecanol 
• 219719-89-8 (2R,4S)-4-nonyl-2-phenyl-1,3-dioxane 
• 72229-32-4 (2R,4R)-2-phenyl-4-(tosyloxy)methyl-1,3-dioxane 
• 17049-49-9 octylmagnesium bromide 

Relevant academic research and scientific papers

Total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide, a new biologically active δ-lactone produced by Seiridium unicorne

The first total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5- olide (1), a new biologically active δ-lactone produced by Seiridium unicome, was accomplished from (R)-malic acid. In connection with the determination of the absolute configuration of 1, (2R,3S,5R)-(+)-2,3- dihydroxytetradecan-5-olide (ent-1) was also synthesized from D-glucose.

Isolation, structural determination, and total synthesis of a new biologically active δ-lactone produced by Seiridium unicorne

The structure of a new biologically active δ-lactone, produced by Seiridium unicorne, was determined to be (2S,3R,5S)-(-)-2,3- dihydroxytetradecan-5-olide. The relative configuration was elucidated from NMR experiments. The synthesis of the enantiomer from D-glucose revealed the absolute configuration. The total synthesis of the natural form was also achieved from (R)-malic acid.