22555-67-5

Upstream product

• 110-93-0 6-Methyl-hept-5-en-2-on 
• 7484-37-9 (3-phenylpropyl)triphenylphosphonium bromide 
• 20536-36-1 neryl chloride 
• 6921-34-2 benzylmagnesium chloride 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 100-44-7 benzyl chloride 
• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 1309466-61-2 C₁₆H₃₁O₃PS 
• 1589-82-8 phenylmagnesium bromide 
• 106-24-1 Geraniol 
• 74408-52-9 geraniol acetate 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 637-59-2 1-Bromo-3-phenylpropane 
• 6138-90-5 trans-geranyl bromide 

Relevant academic research and scientific papers

Design, synthesis and anthelmintic activity of 7-keto-sempervirol analogues

The plant-derived, diterpenoid 7-keto-sempervirol was recently reported to display moderate activity against larval stages of Schistosoma mansoni (IC50 = 19.1 μM) and Fasciola hepatica (IC50 = 17.7 μM), two related parasitic blood and liver flukes responsible for the neglected tropical diseases schistosomiasis and fascioliasis, respectively. Here, we aimed to increase the potency of 7-keto-sempervirol by total synthesis of 30 structural analogues. Subsequent screening of these new diterpenoids against juvenile and adult lifecycle stages of both parasites as well as the human HepG2 liver cell line and the bovine MDBK kidney cell line revealed structure-activity relationship trends. The most active analogue, 7d, displayed improved dual anthelmintic activity over 7-keto-sempervirol (IC50 ≈ 6 μM for larval blood flukes; IC50 ≈ 3 μM for juvenile liver flukes) and moderate selectivity (SI ≈ 4–5 for blood flukes, 8–13 for liver flukes compared to HepG2 and MDBK cells, respectively). Phenotypic studies using scanning electron microscopy revealed substantial tegumental alterations in both helminth species, supporting the hypothesis that the parasite surface is one of the main targets of this family of molecules. Further modifications of 7d could lead to greater potency and selectivity metrics resulting in a new class of broad-spectrum anthelmintic.

Alkyldisulfanium salts: Isolable, electrophilic sulfur reagents competent for polyene cyclizations

Tools that can effect electrophilic sulfur-promoted cation-π cyclizations are generally lacking, especially using alkylsulfide-based reagents. Herein we report that combining three different 1,2-dithioethers with Cl2 and SbCl5 generates isolable alkyldisulfanium salts that can effect such reactions. These new reagents can install -SMe, -SEt, and -SCH2CH2CF3 in modest, moderate, or good yield on diverse frameworks, including polyenes that terminate with electron-deficient groups. We also show that reagents such as dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) can accomplish similar chemistry.

Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation

An efficient strategy to synthesize the western part of phainanoids is reported. The benzofuranone-based 4,5-spirocyclic motif is constructed diastereoselectively via a palladium-catalyzed intramolecular alkenylation. The computational study suggests that

Accessing brominated natural product motifs using phosphoramidite catalysis

This article describes the application of a first-generation phosphoramidite catalyst to the construction of the most commonly encountered subunits of bromine-containing natural products. The process is compared with previous efforts, and is found to be complementary to existing methods. Application of the process enables bromocarbocyclisations, bromoetherifications, and bromoallene formation using the common laboratory reagent N-bromosuccinimide.

Highly enantioselective proton-initiated polycyclization of polyenes

This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantioselective proton-initiated polycyclization promoted by the 1:1 complex of o,o′-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.

Cu(I)-catalyzed, α-selective, allylic alkylation reactions between phosphorothioate esters and organomagnesium reagents

Regiocontrol of allylic alkylation reactions involving hard nucleophiles remains a significant challenge and continues to be an active area of research. The lack of general methods in which α-alkylation is favored underscores the need for the development of new processes for achieving this type of selectivity. We report that Cu(I) catalyzes the allylic substitution of phosphorothioate esters with excellent α-regioselectivity, regardless of the nature of the Grignard reagent that is used. To the best of our knowledge, the Cu-catalyzed allylic alkylation of phosphorothioate esters has never been described. We have also developed a simple protocol for inducing high α selectivity starting from secondary allylic halides. This is accomplished by using sodium phosphorothioates as an additive.

A two-step mimic for direct, asymmetric bromonium- and chloronium-induced polyene cyclizations

Although direct, asymmetric, halonium-induced cyclizations have proven difficult to achieve in the absence of enzymes, this report provides a two-step alternative based on reacting polyenes with chiral mercury(II) complexes to afford a number of polycyclic organomercurials that can be subsequently converted, with retention, into their corresponding chlorine, bromine, and iodine derivatives in good yield and enantioselectivity. A five-step asymmetric total synthesis of the natural product 4-isocymobarbatol is also described.

Et2SBr.SbCl5Br: An effective reagent for direct bromonium-induced polyene cyclizations

It's all about reactivity: Although bromonium-induced cation-π cyclizations are commonly utilized by nature to fashion six-membered rings from a diverse set of polyene precursors, no general laboratory method exists that can achieve the same breadth of substrate scope. An easily synthesized and handled reagent is described (see scheme) that is capable of directly, broadly, and rapidly effecting such reactions in good yield with a variety of geraniol, farnesol, and nerol derivatives.

Indium tribromide-promoted arene-terminated epoxy olefin cyclization

An arene-terminated epoxy olefin cyclization was promoted by a water-tolerant Lewis acid to give tri- and tetracyclic 3β-hydroxy terpenoids and steroid derivatives in 57 and 37% yields, respectively, per new formed ring up to 75%. The Royal Society of Chemistry.