607376-01-2

Upstream product

• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 121651-02-3 (2S,3R)-2-formyl-3-phenyloxirane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-55-2 3-phenyl-propenal 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 

Downstream Products

• 1298016-15-5 C₂₅H₂₄O₅ 
• 607376-08-9 ethyl 3,4-dihydroxy-5-phenyl-(2S,3R,4R,5S)-tetrahydro-2-furancarboxylate 
• 607376-02-3 ethyl 2,2-dimethyl-6-phenyl-(3aS,4R,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxole-4-carboxylate 

Relevant academic research and scientific papers

An atom-economic synthesis of bicyclo[3.1.0]hexanes by rhodium N-heterocyclic carbene-catalyzed diastereoselective tandem hetero-[5 + 2] cycloaddition/claisen rearrangement reaction of vinylic oxiranes with alkynes

The first synthetic application of a vinylic oxirane as a heteroatom-containing five-atom component in transition-metal-catalyzed cycloaddition reactions is reported. A new, efficient, diastereoselective tandem intramolecular hetero-[5 + 2] cycloaddition/Claisen rearrangement of vinylic oxirane-alkyne substrates that uses a rhodium NHC complex and provides strategically novel, atom-economic, regiospecific, and diastereoselective access to [3.1.0] bicyclic products has been developed.

Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone

A flexible stereoselective route to synthesize both enantiomers of the highly functionalized substituted tetrahydrofurans and α,β- unsaturated-δ-lactones, goniothales diol, altholactone, and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulfonic acid.

A concise and stereoselective synthesis of both enantiomers of altholactone and isoaltholactone

A concise and flexible stereoselective route to synthesize both enantiomers of the highly functionalized α,β-unsaturated-δ-lactones, altholactone and isoaltholactone, from readily available cinnamyl alcohol is described. This approach derived its asymmetry from Sharpless catalytic asymmetric epoxidation and Sharpless asymmetric dihydroxylation reactions. The resulting diols were produced in high enantiomeric excess and were cyclized in a stereoselective manner in the presence of a catalytic amount of camphor sulphonic acid.