51148-68-6Relevant academic research and scientific papers
General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form
Chung, Won-Jin,Carlson, Joseph S.,Vanderwal, Christopher D.
, p. 2226 - 2241 (2014/04/03)
A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and 11 steps, respectively.
A relay ring-opening/double ring-closing metathesis strategy for the bicyclic macrolide-butenolide core structures
Halle, Mahesh B.,Fernandes, Rodney A.
, p. 63342 - 63348 (2015/02/19)
A concise strategy has been developed for the synthesis of the bicyclic macrolide-butenolide core structures of various natural products with the macrolide ring size ranging from 12- to 16-membered. The bicyclic structure was easily assembled using the relay ring-opening/double ring-closing metathesis strategy. An efficient synthesis of (±)-desmethyl manshurolide has been achieved as an application of this strategy. This journal is
Design, chemical synthesis, and in vitro biological evaluation of simplified estradiol-adenosine hybrids as inhibitors of 17β-hydroxysteroid dehydrogenase type 1
Berube, Marie,Poirier, Donald
scheme or table, p. 1180 - 1199 (2009/12/01)
A series of estradiol (E2) derivatives were designed to interact with, both the substrate- and the cofactor-binding sites of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). These analogues of potent E2-adenosine hybrid inhibitor EM-1745, where the adenosine moiety was replaced by a more stable benzene derivative, were synthesized from estrone using alkene cross-metathesis and Sonogashira coupling reactions as key steps. In vitro biological evaluation of these steroid derivatives revealed that a spacer of 13 methylenes, between the 16β-position of E2 and the adenosine mimic bearing a carboxylic acid, group, gave the best inhibition of 17β-HSD1.
Semivolatile and volatile compounds in combustion of polyethylene
Font, Rafael,Aracil, Ignacio,Fullana, Andrés,Conesa, Juan A.
, p. 615 - 627 (2007/10/03)
The evolution of semivolatile and volatile compounds in the combustion of polyethylene (PE) was studied at different operating conditions in a horizontal quartz reactor. Four combustion runs at 500 and 850°C with two different sample mass/air flow ratios and two pyrolytic runs at the same temperatures were carried out. Thermal behavior of different compounds was analyzed and the data obtained were compared with those of literature. It was observed that α,ω-olefins, α-olefins and n-paraffins were formed from the pyrolytic decomposition at low temperatures. On the other hand, oxygenated compounds such as aldehydes were also formed in the presence of oxygen. High yields were obtained of carbon oxides and light hydrocarbons, too. At high temperatures, the formation of polycyclic aromatic hydrocarbons (PAHs) took place. These compounds are harmful and their presence in the combustion processes is related with the evolution of pyrolytic puffs inside the combustion chamber with a poor mixture of semivolatile compounds evolved with oxygen. Altogether, the yields of more than 200 compounds were determined. The collection of the semivolatile compounds was carried out with XAD-2 adsorbent and were analyzed by GC-MS, whereas volatile compounds and gases were collected in a Tedlar bag and analyzed by GC with thermal conductivity and flame ionization detectors.
A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone
Sinha,Sinha-Bagchi,Keinan
, p. 7789 - 7796 (2007/10/02)
Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2- dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.
INSECT PHEROMONES AND THEIR ANALOGUES. XXXVII. SYNTHESIS OF TETRADEC-11E-ENAL AND OF TETRADEC-11E-EN-1-OL AND ITS ACETATE FROM UNDECENOIC ACID
Odinokov, V. N.,Ishmuratov, G. Yu.,Vakhidov, R. R.,Berg, A. A.,Muslukhov, R. R.,Tolstikov, G. A.
, p. 237 - 240 (2007/10/02)
A stereospecific synthesis has been achieved of tetradec-11E-enal and of tetradec-11E-en-1-ol and its acetate - components of the pheromones of many species of insects of the order Lepidoptera - from the readily available undecenoic acid, using the Knoevenagel reaction and catalytic hydroalumination.
