391232-85-2

Upstream product

• 201230-82-2 carbon monoxide 
• 1198096-76-2 (2S)-1-(benzyloxy)-5-hexene-2,4-diol 
• 391232-78-3 2-allyl-5-benzyloxymethyl-3-phenylcarbonyloxy-(2S,3S,5S)-tetrahydrofuran 
• 391232-77-2 methyl 3-O-benzoyl-5-O-benzyl-3-deoxy-α-D-threo-pentofuranoside 
• 391232-80-7 (2S,3S,5S)-2-allyl-5-((benzyloxy)methyl)-tetrahydrofuran-3-ol 
• 391232-76-1 methyl 5-O-benzyl-3-deoxy-α-D-threo-pentofuranoside 
• 14645-49-9 methyl 2,3-anhydro-5-O-benzyl-α-D-lyxofuranoside 

Relevant academic research and scientific papers

Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran

The total synthesis of the C19 lipid diols 5 and 6, the enantiomers of the anthelmintic marine natural products 1 and 3, is described. Key steps in the divergent syntheses include a syn selective epoxidation of a homoallylic alcohol, a one-pot alkoxypalladation-carbonylation-lactonisation reaction sequence and a DMEAD promoted Mitsunobu inversion.

An expedient synthesis of 2,5-disubstituted-3-oxygenated tetrahydrofurans

Single enantiomer 2,5-disubstituted-3-oxygenated tetrahydrofurans are synthesized in as little as four steps from a commercially available epoxide. The key steps are homoallylic alcohol epoxidation, palladium-catalysed alkoxy-carbonylation-lactonisation and Mitsunobu inversion. The protocol is applied to the formal total syntheses of (+)-kumausallene, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol and the core of lytophilippine A.