89726-69-2

Upstream product

• 83160-44-5 (3aR,7S,7aR)-7-Allyl-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 100-51-6 benzyl alcohol 
• 103773-81-5 1-O-benzyl-2,3-isopropylidene-L-lyxopyranose 
• 5329-50-0 1-O-benzyl-L-lyxose 
• 89726-66-9 Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester 
• 87-72-9 L-arabinofuranose 

Downstream Products

• 97997-35-8 Methanesulfonic acid 2-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethyl ester 
• 89726-70-5 (3aR,7S,7aR)-7-(2-Benzenesulfonyl-ethyl)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 89726-71-6 (4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol 
• 89726-72-7 Methanesulfonic acid (2S,3S)-1-[1-benzenesulfonyl-2-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyl ester 
• 71980-98-8 pseudomonic acid C 

Relevant academic research and scientific papers

Pseudomonic Acid C from L-Lyxose

Full details of the total synthesis of pseudomonic acid C from L-lyxose are described.Key features of the approach involve feee-radical allylation for stereoselective C-C bond formation at C4 of lyxose, Frater alkylation to generate correct stereochemistry at C12 and C13, and stereoselective intramolecular Michael addition to establish the correct stereochemistry of the "anomeric" appendage.

Total Synthesis of Pseudomonic Acid C

A convergent total synthesis of pseudomonic acid C from L-lyxose is described in which a highly stereoselective free-radical C-C bond construction plays a key role.