691882-92-5

Upstream product

• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 691882-87-8 [3aR,4R,5S,6aS]-3-hydroxymethylene-5-methyl-4-(2-trimethylsilanylethoxymethoxymethyl)hexahydro-cyclopenta[b]furan-2-one 
• 691882-91-4 [3aR,4R,5S,6aS]-5-methyl-4-(2-trimethylsilanylethoxymethoxymethyl)hexahydro-cyclopenta[b]furan-2-one 
• 691882-90-3 [3aR,4S,5R,6R,6aR]-4-hydroxymethyl-6-iodo-5-methyl-hexahydro-cyclopenta[b]furan-2-one 
• 691882-88-9 [3aR,4R,5S,6aS]-4-hydroxymethyl-5-methyl-hexahydro-cyclopenta[b]furan-2-one 
• 691882-89-0 [4aS,5Z,7S,7aR]-7-methyl-4,4a,7,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one 
• 371778-63-1 acetic acid 2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-4-ylmethyl ester 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 691882-86-7 [3E,3aS,4R,5S,6aS]-4-hydroxymethyl-5-methyl-3-([2R,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxymethylene)hexahydro-cyclopenta[b]furan-2-one 
• 691882-93-6 [2aS,4S,4aR,7R,7aS,7bS]-4-methyl-7-([2S,3R,4S,5R,6R]-3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-yloxy)octahydro-2,6-dioxa-cyclopenta[cd]inden-1-one 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of Semperoside A

A versatile and concise strategy has been developed (Scheme 1) for the enantioselective synthesis of semperoside A 1 which is endowed with an unusually glucosylated iridane structure. The crucial step was a Hg(II)-mediated electrophilic heteroatom cyclization of β-glucoside 4 that readily led to the iridane skeleton while installing the C-2 and C-3 stereocenters with complete stereocontrol. This expeditious route is unprecedented among synthetic approaches to iridoid glycosides and smoothly overcomes the hemiacetals glucosidation issue. The present inaugural total synthesis of semperoside A was achieved in 10 steps and 17% overall yield from the enantiomerically pure lactone 8, thus proving the absolute stereochemistry of 1 unequivocally. Copyright