55393-33-4

Upstream product

• 109-65-9 1-bromo-butane 
• 86-93-1 1-Phenyl-1H-tetrazole-5-thiol 
• 71-36-3 butan-1-ol 
• 108106-71-4 2,2,2-trichloro-acetimidic acid butyl ester 
• 542-69-8 1-iodo-butane 

Downstream Products

• 519002-87-0 5-(butane-1-sulfonyl)-1-phenyl-1H-tetrazole 

Relevant academic research and scientific papers

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.

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

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.

Alkylation of thiols with trichloroacetimidates under neutral conditions

Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

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.