155690-26-9

Upstream product

• 100-39-0 benzyl bromide 
• 57445-90-6 pent-4-ene-1,3-diol 
• 184376-29-2 (S)-3-(benzyloxy)pent-4-en-1-ol 
• 155690-33-8 (S)-3-hydroxy-4-pentenyl triphenylmethyl ether 
• 184089-76-7 3-hydroxy-4-pentenyl triphenylmethyl ether 
• 155750-79-1 (S)-3-(benzyloxy)-4-pentenylpropanedioic acid dimethyl ester 

Downstream Products

• 82093-34-3 (-)(2S,3R)-cyclosarkomycin 
• 160023-07-4 (3aS,4S,6aR)-4-Benzyloxy-hexahydro-cyclopenta[c]furan-1-one 

Relevant academic research and scientific papers

Diastereoselective iodocarbocyclization reaction of 2- or 3-oxy-4-pentenylmalonate derivatives

1,2- Or 1,3-asymmetric induction in the iodocarbocyclization reaction of 4-pentenylmalonate derivatives having a stereogenic center at an allylic or a homoallylic position has been investigated. The iodocarbocyclization reactions of 3-oxy-4-pentenylmalonate derivatives proceeded with high cis-selectivity through stereoelectronic control of the oxygenated substituent at an allylic position. In the reaction of (S)-2-siloxy-4-pentenylmalonate, an excellent diastereoselectivity was achieved through the utilization of double stereodifferentiation with a chiral titanium catalyst. Furthermore, as an application of the present reaction, the asymmetric syntheses of cyclosarkomycin and a synthetic intermediate of brefeldin A from optically pure 2- and 3-oxy-4-pentenylmalonate derivatives are also described.

DIASTEREOSELECTIVE IODOCARBOCYCLIZATION OF 4-PENTENYLMALONATE DERIVATIVES: APPLICATION TO CYCLOSARKOMYCIN SYNTHESIS

The iodocarbocyclization of 4-pentenylmalonate 1 having a substituent at the 2 or 3 position effectively proceeded by treating 1 with I2 and Ti(OtBu)4 in the presence of CuO.Stereoelectronic effect of the substituent at allylic position on diastereoselect