1003600-48-3

Upstream product

• 1357379-96-4 1,2-dideoxy-5,6-O-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 
• 1357379-97-5 1,2-dideoxy-5,6-(1-methylethylidene)-3-O-(triethylsilyl)-D-arabino-hex-1-enitol 4-(prop-2-enoate) 
• 1357379-98-6 (1S,2R)-1-[(1R)-1,2-dihydroxyethyl]-2-hydroxybut-3-en-1-yl prop-2-enoate 
• 1357379-99-7 (1S,2R)-2-(acetyloxy)-1-[ (1R)-1-(acetyloxy)-2-(benzyloxy)ethyl]but-3-en-1-yl prop-2-enoate 
• 98-88-4 benzoyl chloride 
• 506-96-7 Acetyl bromide 
• 1239353-07-1 C₁₄H₁₄O₆ 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 37776-15-1 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 35958-64-6 3,5,6-Tri-O-benzyl-D-glucofuranose 

Relevant academic research and scientific papers

Total synthesis of (?)-cleistenolide and formal synthesis of herbarumin I via a diastereoselective modulable allylation

A modulable tin based allylation method for the synthesis of 1,2,3-triols is described. The optimization of the reaction was aided by 1H and 119Sn low temperature NMR spectroscopic investigations, which support the formation of two c

Stereoselective total synthesis of (-)-cleistenolide

A facile stereoselective total synthesis of cleistenolide (1) from the natural chiral template d-arabinose has been achieved in eight steps and 49% overall yield, employing key steps including Wittig olefination, selective 1,3-trans-acetal formation, and modified Yamaguchi esterification.

Synthesis, antiproliferative activity and SAR analysis of (?)-cleistenolide and analogues

A new, modified total synthesis of (?)-cleistenolide (1) and sixteen new analogues or derivatives was achieved starting from commercially available 1,2-O-isopropylidene-α-D-glucofuranose. The synthesis of 1 proceeds in six steps and 67% overall yield, usi

Synthesis and antimicrobial activity of (?)-cleistenolide and analogues

Using the “chiral pool” approach, two modified total syntheses of the biologically active δ-lactone cleistenolide (1) have been achieved starting from D-glucose. These approaches also enabled the preparation of novel analogues and derivatives of natural product 1. The applied strategy for the synthesis of 1 involves: the initial degradation of the chiral precursor for a single C-atom, C2-fragment chain extension using Z-selective Wittig reaction, and the final δ-lactonization. All tested cleistenolide analogues displayed antimicrobial activity against a panel of nine microbial strains, most of them superseding the activity of cleistenolide itself, and, in some cases, coming close in value to the observed minimal inhibitory concentrations of chloramphenicol. Increased lipophilicity of the derivatives and the non-sterically congested conjugated lactone moiety were a prerequisite for analogues with high inhibitory activity against S. aureus and, in general, Gram-positive bacteria.

New antitumour agents with α,β-unsaturated δ-lactone scaffold: Synthesis and antiproliferative activity of (?)-cleistenolide and analogues

A stereoselective total synthesis of (?)-cleistenolide (1) from D-glucose has been achieved. This new approach for the synthesis of (?)-cleistenolide and analogues involves a one-C-atom degradation of the chiral precursor, (Z)-selective Wittig olefination, followed by the final δ-lactonisation. Synthesized compounds showed potent growth inhibitory effects against selected human tumour cell lines, especially 2,4,6-trichlorobenzoyl derivative 12, which in the culture of MDA-MB 231 cells displayed the highest activity (IC500.02?μM) of all compounds under evaluation. A preliminary SAR study reveals the structural features that are beneficial for antiproliferative activity of synthesized δ-lactones, such as presence of either electron-withdrawing or electron-donating substituents in the aromatic ring, as well as the presence of cinnamoyl functionality instead of benzoyl group at the O-7 position.

A concise total synthesis of cleistenolide

A concise total synthesis of cleistenolide has been achieved from D-glucose. The synthesis of cleistenolide proceeds in six steps from D-glucose diacetonide in 42.5% overall yield. Selective benzoylation and Still-Gennari olefination are the key reactions involved in the synthesis.

Enantioselective construction of 6-substituted-α,β-unsaturated- δ-lactone: Total synthesis of anti-bacterial agent (-)-cleistenolide

An efficient and straightforward stereoselective synthesis of α,β-unsaturated lactone (1) cleistenolide is described. The synthesis was started from commercially available d-tartaric acid and completed within 13 steps with an overall yield of 7.92%. The cis-olefin was generated from Still-Gennari protocol and one of the hydroxyl groups was from dihydroxylation methodology. All the reactions were very clean and the products were obtained in very good yields.

A simple and efficient stereoselective synthesis of (-)-cleistenolide

A simple and straightforward stereoselective synthesis of α,β-unsaturated δ-lactone, (-)-cleistenolide has been accomplished in 10 steps in an overall yield of 19%, starting from inexpensive and commercially available starting materials, respectively. This linear synthesis utilizes Sharpless asymmetric dihydroxylation, sulfur ylide mediated epoxide opening followed by ring-closing metathesis (RCM) for the formation of six-membered lactone ring as the key step sequence.

The stereoselective total synthesis of (-)-cleistenolide

The stereoselective total synthesis of (-)-cleistenolide is described employing the Barbier allylation, MacMillan α-hydroxylation, Stille-Gennari olefination, and CeCl3·7H2O mediated lactonization as key steps.

Total synthesis of (-)-cleistenolide

The total synthesis of (-)-cleistenolide, a novel natural product recently isolated from the annonaceae species cleistochlamys kirkii oliver, is described. The synthesis proceeds starting from easily accessible d-manitol using a selective benzoylation, a