129042-95-1

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 247164-62-1 methyl (R)-[(2,2'-bishydroxy-1,1'-binaphthyl)phosphonyl]acetate 
• 179042-34-3 (2,6-Dimethyl-4-oxo-3,5-dioxa-4λ⁵-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-acetic acid methyl ester 
• 20620-59-1 5-phenyl-n-valeric acid methyl ester 
• 1007586-73-3 methyl 2-diazo-5-phenylpentanoate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 96-32-2 bromoacetic acid methyl ester 
• 1070879-04-7 C₂₁H₁₉O₅PS 

Downstream Products

• 20620-59-1 5-phenyl-n-valeric acid methyl ester 
• 75553-23-0 5-phenylpenta-2-en-1-ol 
• 24271-22-5 5-phenyl-2(E)-pentenoic acid 
• 138034-94-3 (Z)-5-Phenylpent-2-enoic Acid 

Relevant academic research and scientific papers

Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis

Direct α-functionalization of NH2-free glycinates with relatively weak electrophiles such as α,β-unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5 d as a carbonyl catalyst, direct asymmetric conjugated addition at the α-C of glycinate 1 a with α,β-unsaturated esters 2 has been successfully realized, to produce various chiral pyroglutamic acid esters 4 in 14–96 % yields with 81–97 % ee's after in situ lactamization. The trans and cis diastereomers can be obtained at the same time by chromatography and both of them can be easily converted into chiral 4-substituted pyrrolidin-2-ones such as Alzheimer's drug Rolipram (11) with the same absolute configuration via tert-butyl group removal and subsequent Barton decarboxylation.

Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.

Cascade reaction including a formal [5?+?2] cycloaddition by use of alkyne-Co2(CO)6 complex

A new cascade reaction including formal [5 + 2] cycloaddition was developed. Treatment of homocinnamyl alcohol and Co2(CO)6-complexed arylpropynal with BF3·OEt2 resulted in the generation of hydrobenzocyclohepta

Zwitterionic phosphonium sulfonates as easily phase-separable ion-tagged wittig reagents

(Chemical Equation Presented) Zwitterionic phosphonium sulfonates 3, conveniently derived from TPPMS (1), can be used as Wittig reagents in solution. The excess reagents and byproduct TPPMSO (6) can be easily separated from the product alkenes by simple precipitation with a less polar solvent. The alkenes thus obtained were often sufficiently pure without chromatographic purification. A one-pot protocol for the synthesis of α,β-unsaturated esters has been developed and appears to be convenient.

Total synthesis of bryostatin 2

The total synthesis of the marine macrolide bryostatin 2 is described. The synthesis plan relies on aldol and directed reduction steps in order to construct the anti-1,3-diol array present in each of the principal subunits (A, B, and C). These fragments were coupled using a Julia olefination and subsequent sulfone alkylation. A series of functionalization reactions provided a bryopyran seco acid, which was macrolactonized under Yamaguchi conditions. Installation of the two enoate moieties took advantage of asymmetric phosphonate and aldol condensation strategies. Reduction of the C20 ketone and simple protecting group operations then completed the synthesis of bryostatin 2. This flexible approach should provide access to a series of new analogues of this clinically important marine natural product.