160732-08-1

Upstream product

• 1589-82-8 phenylmagnesium bromide 
• 4538-50-5 methyl (2S)-glycidate 
• 169302-19-6 (2S,3S)-3,4-epoxy-2-hydroxy-1-phenylbutane 
• 6052-66-0 1-phenyl-3-buten-2-ol 
• 122-78-1 phenylacetaldehyde 
• 169302-23-2 (2S,3S)-1,2-epoxy-4-phenylbutan-3-ol 
• 766-04-1 benzyllithium 
• 4861-85-2 isopropyl phenylacetate 
• 119373-39-6 1-benzylcyclopropan-1-ol 
• 6052-66-0 1-phenyl-but-3-en-2-ol 

Downstream Products

• 1440943-34-9 (1R,2R,4S,5S)-2-(hydroxymethyl)-4-phenylbicyclo[3.2.1]oct-6-en-3-one 
• 1440943-36-1 (1S,2R,4S,5R)-2-(hydroxymethyl)-4-phenylbicyclo[3.2.1]oct-6-en-3-one 

Relevant academic research and scientific papers

A short synthesis of (+)-(S)-kurasoin B

A short efficient enantioselective synthesis leading directly to (+)-(S)-kurasoin B has been achieved in 5 steps and 25% overall yield from (2E)-ethyl-4-phenylbut-2-enoate using Sharpless asymmetric dihydroxylation and CH3NO2-assiste

Enantioselective One-Pot Synthesis of α,β-Epoxy Ketones via Aerobic Oxidation of Cyclopropanols

An efficient, mild, and environmentally benign method was developed for the asymmetric synthesis of 2-oxyranyl ketones from easily available tertiary cyclopropanols. The one-pot protocol includes the aerobic oxidation of cyclopropanol derivatives catalyzed by Mn(III) complexes followed by the poly-l-leucine-assisted stereoselective elimination of water from the intermediate peroxides with DBU to afford the corresponding epoxy ketones in high yields and good-to-excellent enantioselectivities (up to 97%).

Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes

A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl). Copyright

Total syntheses of kurasoins A and B, novel protein farnesyltransferase inhibitors, and absolute structures of kurasoins A and B

Asymmetric total syntheses of kurasoins A (1) and B (2), recently discovered protein farnesyltransferase (PFTase) inhibitors, have been achieved in seven steps from 2-(4-hydroxyphenyl)ethanol via the stereospecific alkylation of the chiral epoxide ((-)-7) and in four steps from phenylacetaldehyde via the coupling reaction of the chiral epoxide ((-)- 13) with indole, respectively. The synthesis defined the (3S) absolute configuration of 1 and 2. The stereochemistry of the hydroxy group is important for eliciting PFTase inhibition.

An efficient route to α,β-epoxy ketones of high enantiomerical purity

Acylepoxides were obtained in high enantiomeric purity (ee = 92-99%) by addition of organolithium or Grignard reagents to enantiomerically pure methyl or ethyl 2,3-epoxypropanoates at low temperature (-85°C).