519002-87-0

Upstream product

• 55393-33-4 5-(butylthio)-1-phenyl-1H-tetrazole 
• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 

Downstream Products

• 1301262-04-3 C₁₈H₁₈N₈O₂S 
• 98411-61-1 (Z)-1-chloro-4-(hex-2-en-2-yl)benzene 
• 98411-58-6 (E)-1-chloro-4-(hex-2-en-2-yl)benzene 
• 18654-74-5 (E)-1-chloro-4-(pent-1-en-1-yl)benzene 
• 1301261-93-7 (S,E)-((hept-3-en-2-yloxy)methyl)benzene 
• 60669-43-4 (E)-hept-3-enylbenzene 
• 60669-42-3 (Z)-hept-3-enylbenzene 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of (+)-Majusculoic Acid via a Dimerization-Dedimerization Strategy and Absolute Configuration Assignment

The first total synthesis of (+)-majusculoic acid, the enantiomer of naturally occurring antifungal cyclopropane fatty acid (-)-majusculoic acid, was accomplished in 13 steps, leading to the assignment of the absolute configuration of the natural product.

Synthesis of the Cyanobacterial Antibiotics Anaephenes A and B

The first syntheses of the antibacterial natural products anaephenes A (1) and B (2) are reported. Both natural products were synthesized in five linear steps from commercially available tert-butyl(3-iodophenoxy)dimethylsilane. Key steps for the synthesis

The Discovery and Structure-Activity Evaluation of (+)-Floyocidin B and Synthetic Analogs

Tuberculosis represents one of the ten most common courses of death worldwide and the emergence of multidrug-resistant M. tuberculosis makes the discovery of novel anti-tuberculosis active structures an urgent priority. Here, we show that (+)-floyocidin B representing the first example of a novel dihydroisoquinoline class of fungus-derived natural products, displays promising antitubercular hit properties. (+)-Floyocidin B was identified by activity-guided extract screening and its structure was unambiguously determined by total synthesis. The absolute configuration was deduced from a key synthesis intermediate by single crystal X-ray diffraction analysis. A hit series was generated by the isolation of further natural congeners and the synthesis of analogs of (+)-floyocidin B. Extensive biological and physicochemical profiling of this series revealed first structure-activity relationships and set the basis for further optimization and development of this novel antitubercular scaffold.

Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B

The combination of a highly stereoselective tethered olefin metathesis reaction and a Julia-Kocienski olefination is presented as a strategy for the synthesis of conjugated polyenes with at least one Z-configured Ca?C bond. The strategy is exemplified by the synthesis of the marine natural product (+)-bretonin B.

Simple protocol for enhanced (E)-selectivity in Julia-Kocienski reaction

A short and efficient Julia-Kocienski olefination protocol, based upon the use of chelating agents (18-crown-6 or TDA-1 for K+; 12-crown-4 or HMPA for Li+), was developed. This protocol enhances the (E)-selectivity of the reaction an

Sanglifehrin-cyclophilin interaction: Degradation work, synthetic macrocyclic analogues, x-ray crystal structure, and binding data

Sanglifehrin A (SFA) is a novel immunosuppressive natural product isolated from Streptomyces sp. A92-308110. SFA has a very strong affinity for cyclophilin A (IC50 = 6.9 ± 0.9 nM) but is structurally different from cyclosporin A (CsA) and exerts its immunosuppressive activity via a novel mechanism. SFA has a complex molecular structure consisting of a 22-membered macrocycle, bearing in position 23 a nine-carbon tether terminated by a highly substituted spirobicyclic moiety. Selective oxidative cleavage of the C26 = C27 exocyclic double bond affords the spirolactam containing fragment 1 and macrolide 2. The affinity of 2 for cyclophilin (IC50 = 29 ± 2.1 nM) is essentially identical to SFA, which indicates that the interaction between SFA and cyclophilin A is mediated exclusively by the macrocyclic portion of the molecule. This observation was confirmed by the x-ray crystal structure resolved at 2.1 A of cyclophilin A complexed to macrolide 16, a close analogue of 2. The x-ray crystal structure showed that macrolide 16 binds to the same deep hydrophobic pocket of cyclophilin A as CsA. Additional valuable details of the structure-activity relationship were obtained by two different chemical approaches: (1) degradation work on macrolide 2 or (2) synthesis of a library of macrolide analogues using the ring-closing metathesis reaction as the key step. Altogether, it appears that the complex macrocyclic fragment of SFA is a highly optimized combination of multiple functionalities including an (E,E)-diene, a short polypropionate fragment, and an unusual tripeptide unit, which together provide an extremely strong affinity for cyclophilin A.