160023-07-4

Upstream product

• 100-39-0 benzyl bromide 
• 57445-90-6 pent-4-ene-1,3-diol 
• 163015-30-3 ((1S,2S,6R,7R,8S,9R)-9-Benzyloxy-4,4-dimethyl-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-8-yl)-methanol 
• 163015-31-4 (1R,2R,3S,4R,5R,6S)-5-Benzyloxy-6-hydroxymethyl-bicyclo[2.2.1]heptane-2,3-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 
• 155690-26-9 (S)-tetrahydro-6-(benzyloxy)-3-oxo-1H-cyclopentafuran-3a(3H)-carboxylic acid methyl ester 
• 155750-79-1 (S)-3-(benzyloxy)-4-pentenylpropanedioic acid dimethyl ester 
• 163061-62-9 (3aS,4R,5S,6aR)-4-Benzyloxy-1-oxo-hexahydro-cyclopenta[c]furan-5-carboxylic acid 

Downstream Products

• 82093-34-3 (-)(2S,3R)-cyclosarkomycin 

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.

Access to an Optically Pure Cyclosarkomycin by Conversion of the Endo Adduct of (R)-Allene 1,3-Dicarboxylate and Cyclopentadiene

The enantioselective synthesis of (-)-cyclosarkomycin is accomplished using the endo 1:1 adduct of (R)-allene 1,3-dicarboxylate and cyclopentadiene.

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