184481-19-4

Upstream product

• 184481-18-3 (5S,3R,4R)-2-(phenylmethoxy)perhydro-2H-pyran-3,4,5-triol 
• 77-76-9 2,2-dimethoxy-propane 
• 100-51-6 benzyl alcohol 
• 67-64-1 acetone 
• 87-72-9 D-lyxose 

Downstream Products

• 184481-20-7 1-<(6S,1R,2R)-8,8-dimethyl-4,7,9-trioxa-5-(phenylmethoxy)bicyclo<4.3.0>non-2-yloxy>-1,1,2,2-tetramethyl-1-silapropane 
• 1201848-90-9 C₁₈H₂₆O₆ 
• 184481-28-5 methyl 6-<(4S,7S,7aS,3aR)-7-hydroxy-2,2-dimethyl-4-<(phenylmethoxy)amino>-6-phenylthio-2,3,4,7,3a,7a-hexahydro-1,3-dioxainden-5-yl>-2H-benzo1,3-dioxolane-5-carboxylate 
• 184481-25-2 6-((3R)-3-<(4R,5R)-5-<2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-(1,1,2,2-tetramethyl-1-silapropoxy)prop-1-ynyl)-2H-benzo1,3-dioxolene-5-carbaldehyde 
• 184481-27-4 methyl 6-((3R)-3-<(4S,5R)-5-<2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-hydroxyprop-1-ynyl)-2H-benzo1,3-dioxolene-5-carboxylate 
• 184481-29-6 (2aS,2R,5aR,5bR)-2-hydroxy-4,4-dimethyl-1-phenylthio-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-j>1,3-dioxolano<4,5-c>phenanthridin-7-one 
• 184481-26-3 6-((3R)-3-<(4S,5R)-5-<2-aza-2-(phenylmethoxy)vinyl>-2,2-dimethyl(1,3-dioxolan-4-yl)>-3-hydroxyprop-1-ynyl)-2H-benzo1,3-dioxolene-5-carbaldehyde 
• 184481-24-1 1-(1-<5-<2-aza-2-(phenylmethoxy)vinyl>(4R,5R)-2,2-dimethyl(1,3-dioxolan-4-yl)>(1R)prop-2-ynyloxy)-1,1,2,2-tetramethyl-1-silapropane 
• 184481-21-8 2-<5-<2-aza-2-(phenylmethoxy)vinyl>(4R,5R)-2,2-dimethyl(1,3-dioxolan-4-yl)>(2R)-2-(1,1,2,2-tetramethyl-1-silapropoxy)ethan-1-ol 

Relevant academic research and scientific papers

Synthesis of a Resorcylic Acid Lactone (RAL) library using fluorous-mixture synthesis and profile of its selectivity against a panel of kinases

A library of resorcylic acid lactones (RAL) containing a cis-enone moiety targeting kinases bearing a cysteine residue within the ATP-binding pocket was prepared using a fluorous-mixture synthesis and evaluated against a panel of 19 kinases thus providing important structure-activity trends. Two new analogues were then profiled for their selectivity against a panel of 402 kinases providing the broadest evaluation of this pharmacophores' selectivity.

Total syntheses of (-)-lycoricidine, (+)-lycoricidine, and (+)- narciclasine via 6-exo cyclizations of substituted vinyl radicals with oxime ethers

The development of an approach to the total synthesis of the title alkaloids is described. The approach utilizes as the key strategic element a stereoselective 6-exo radical cyclization of a vinyl radical to an O- benzyloxime radical acceptor group. The vinyl radical was itself generated by regioselective addition of phenylthiyl radical to a disubstituted alkyne. The regiochemical issues of such additions, which result in different outcomes with tri-n-butylstannyl radicals and phenylthiyl radicals, are discussed. The first such synthesis described, that of (-)-lycoricidine, proceeded in 14 steps and 11% overall yield from 10 and served to develop the radical chemistry required. A second-generation synthesis, this time of the natural (+) enantiomer, was developed using insights gleaned from the first study and proved much more efficient, providing the target alkaloid in nine steps and 44% overall yield. This approach was then employed in the more demanding case of (+)-narciclasine. Several problems arising due to the more electron rich aromatic moiety present in this structure are described. The synthesis developed to deal with these aspects afforded (+)-narciclasine in 12 steps and 26% overall yield.