128856-71-3

Upstream product

• 764-58-9 (E)-hept-3-ene-1-yne 
• 251959-52-1 (5R,6R)-bis-trimethylsiloxy-2-cyclohexenone 
• 128856-69-9 (2R,3R,5R)-2,3-O-isopropylidene-2,3-dihydroxy-5-(1',3'-E,E-1'-heptadienyl)-cyclohexanone 
• 928-97-2 (E)-3-hexen-1-ol 
• 251959-51-0 (3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-1,5,6-tris-trimethylsilanyloxy-cyclohexene 
• 251959-50-9 (2R,3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3-bis-trimethylsilanyloxy-cyclohexanone 
• 225793-33-9 (5R)-5-(tert-butyldimethylsiloxy)cyclohex-2-enone 
• 75-77-4 chloro-trimethyl-silane 
• 128856-70-2 (2R,3R,5R)-5-((1E,3E)-hepta-1,3-dienyl)-2,3-dihydroxycyclohexanone 

Downstream Products

• 251959-53-2 (2R,3S,5R,6R)-3-((1E,3E)-Hepta-1,3-dienyl)-2-hydroxymethyl-5,6-bis-trimethylsilanyloxy-cyclohexanone 
• 140224-89-1 3-hepta-1,3-dienyl-5,6-dihydroxy-2-hydroxymethylcyclohexanone 

Relevant academic research and scientific papers

Asymmetric synthesis of palitantin from the (5R)-tert-butyldimenthylsiloxy-2-cyclohexenone

(+)-Palitantin (2) has been synthesized in 25% overall yield from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone [(R)-1] where a remarkable diastereoselective cat. OsO4 cis-dihydroxylation of (R)-1 furnished the precursor of the optically pure (5R,6R)-bis-trimethylsiloxy 2-cyclohexenone (7) which underwent highly selectively the 1,4-addition reaction of the 1,3-heptadienyl cyanocuprate to give, after trapping of the corresponding copper enolate with formaldehyde, the target compound.

SYNTHESIS OF (+)-PALITANTIN

(-)-Quinic acid was utilized for the synthesis of (+)-palitantin adopting the chiron approach.Pertinent methodology includes stereocontrolled free-radical deoxygenation, functional group adjustments and an α-keto hydroxymethylation reaction.