203301-81-9

Upstream product

• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 
• 108-24-7 acetic anhydride 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 201472-30-2 (R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol 
• 128075-94-5 (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one 

Downstream Products

• 203302-02-7 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one 
• 203523-09-5 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one 
• 874382-93-1 (1'S,4'R)-1-[5'-tert-butyldiphenylsilyl-2',3'-dideoxy-β-L-ribofuranosyl]-2-methyl-3-benzyloxy-4-pyridinone 
• 874382-95-3 (1'R,4'R)-1-[5'-tert-butyldiphenylsilyl-2',3'-dideoxy-α-L-ribofuranosyl]-2-methyl-3-benzyloxy-4-pyridinone 
• 139594-87-9 amphidinolide F 

Relevant academic research and scientific papers

Total Synthesis of the Marine Macrolide Amphidinolide F

A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.

Synthesis and antiviral evaluation of cyclic and acyclic 2-methyl-3-hydroxy-4-pyridinone nucleoside derivatives

A series of cyclic and acyclic nucleoside analogues derived from 3-hydroxy-4-pyridinone were synthesized using the Vorbrüggen reaction. Iron chelation studies, and antiviral evaluation against a broad panel of viruses, were performed. The pKa value of ligand 25 and the stability constant of the corresponding iron-(III) complex were compared to those of deferiprone. The pFe3+ values were found to be similar. Some compounds showed moderate activity against both wild-type HSV-1 and HSV-2, as well as against a thymidine kinase deficient strain of HSV-1. These results suggest a novel mode of action for this group of nucleoside analogues.

The Utility of Furan-, Pyrrole-, and Thiophene-Based 2-Silyloxy Dienes as Demonstrated by Modular Synthesis of Annonaceous Acetogenin Core Units and Their Pyrrolidine and Thiolane Analogues

We report a modular strategy for obtaining the core units of annonaceous acetogenins and their nitrogen and sulfur analogues, which generates great structural diversity. This synthesis is based on the application of a reiterative vinylogous addition protocol involving a unique triad of silyloxy diene modules, 2-[(tert-butyldimethylsilyl)oxy]furan (TBSOF), N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP), and 2-[(tert-butyldimethylsilyl)oxy]thiophene (TBSOT) and suitable heteroatom-stabilized carbenium ions. By combining TBSOF, TBSOP, and TBSOT nucleophilic synthons with certain tetrahydrofuran, pyrrolidine, and thiolane acceptors, the construction of varied, adjacently linked oligo-heterocyclic motifs related to the core segments of the annonaceous acetogenins is assured. At first, the reliability of the pivotal coupling maneuver was certified, by assembling a collection of 18 model constructs, covering all oxygen, nitrogen, and sulfur heteroatom combinations (i.e., compounds 7-9, 13-15, and 19-21). This uniformed protocol was then suited to forge advanced bis-tetrahydrofuran, bis-pyrrolidine, and bis-thiolane scaffolds encompassing the heterocyclic core portion of various binuclear annonaceous acetogenins and relatives. The utility of this synthesis was demonstrated by the preparation of a repertoire of eight isomeric bis-tetrahydrofuran units, 41-48, two bis-pyrrolidine units, 62 and 63, and four bis-thiolane units, 78-81.