1195-49-9Relevant articles and documents
Aroma Chemical Syntheses with Fencholenic Aldehyde
Schulze, Klaus,Uhlig, Holger
, p. 547 - 560 (1989)
With respect to the molecular requirements on sandalwood aroma chemicals the synthesis of some derivatives of the title compound is described.The synthesis of the new homofencholenic aldehyde affords the connection of the 2,2,4-trimethylcyclopentenylsyste
Total synthesis of the Tiacumicin B (lipiarmycin A3/fidaxomicin) aglycone
Glaus, Florian,Altmann, Karl-Heinz
supporting information, p. 1937 - 1940 (2015/02/19)
Tiacumicin B (lipiarmycin A3, fidaxomicin) is an atypical macrolide antibiotic which is used for the treatment of Clostridium difficile infections. Tiacumicin B is also a potent inhibitor of Mycobacterium tuberculosis, but due to its limited oral bioavailability is unsuitable for systemic therapy. To provide a basis for structure-activity studies that might eventually lead to improved variants of tiacumicin B, we have developed an efficient approach to the synthesis of the tiacumicin B aglycone. The synthesis features a high-yielding intramolecular Suzuki cross-coupling reaction to effect macrocyclic ring closure. Key steps in the synthesis of the macrocyclization precursor were a highly selective, one-pot Corey-Peterson olefination and an ene-diene cross-metathesis reaction. Depending on the reaction conditions, the final deprotection delivered either the fully deprotected tiacumicin B aglycone or partially protected versions thereof.
Synthesis of the atropurpuran A-ring via an organocatalytic asymmetric intramolecular Michael addition
Chen, Huan,Zhang, Dan,Xue, Fei,Qin, Yong
, p. 3141 - 3148 (2013/05/09)
The asymmetric synthesis of the A-ring fragment 2a-b of atropurpuran 1 has been achieved in 15 steps with up to 70% ee via an organocatalytic intramolecular Michael addition of nitroalkene 10. The absolute configuration of the two contiguous carbon center
Discovery of substituted biphenyl imidazoles as potent, bioavailable bombesin receptor subtype-3 agonists
He, Shuwen,Dobbelaar, Peter H.,Liu, Jian,Jian, Tianying,Sebhat, Iyassu K.,Lin, Linus S.,Goodman, Allan,Guo, Cheng,Guzzo, Peter R.,Hadden, Mark,Henderson, Alan J.,Ruenz, Megan,Sargent, Bruce J.,Yet, Larry,Kelly, Theresa M.,Palyha, Oksana,Kan, Yanqing,Pan, Jie,Chen, Howard,Marsh, Donald J.,Shearman, Lauren P.,Strack, Alison M.,Metzger, Joseph M.,Feighner, Scott D.,Tan, Carina,Howard, Andrew D.,Tamvakopoulos, Constantin,Peng, Qianping,Guan, Xiao-Ming,Reitman, Marc L.,Patchett, Arthur A.,Wyvratt Jr., Matthew J.,Nargund, Ravi P.
scheme or table, p. 1913 - 1917 (2010/07/02)
We report SAR studies on a novel non-peptidic bombesin receptor subtype-3 (BRS-3) agonist lead series derived from high-throughput screening hit RY-337. This effort led to the discovery of compound 22e with significantly improved potency at both rodent and human BRS-3.
Synthesis of imines, diimines and macrocyclic diimines as possible ligands, in aqueous solution
Simion, Alina,Simion, Cristian,Kanda, Tadeshige,Nagashima, Satoko,Mitoma, Yoshiharu,Yamada, Tomoko,Mimura, Keisuke,Tashiro, Masashi
, p. 2071 - 2078 (2007/10/03)
Although it is recognized that the presence of water is disadvantageous for imine synthesis, we demonstrate that such synthesis can be effective in completely aqueous media, without any catalyst and under mild conditions. Thus, arylaryl, aryl-alkyl, alkyl-aryl and alkyl-alkyl monoimines as well as a large variety of diimines are obtained by direct condensation of the corresponding carbonyl compounds and amines, in water. The same process is used to synthesize macrocyclic diimines starting from methylene, ethylene, trimethylene and tetramethylene glycol bis(2-formylphenyl ether) and ethylene-, trimethylene- and tetramethylene-diamine, some of these macrocycles being known for their chelating properties.
A Facile Oxidation of Secondary Amines to Imines by Iodosobenzene or by a Terminal Oxidant and Manganese or Iron Porphyrins and Manganese Salen as the Catalysts
Larsen, Jan,Joergensen, Karl Anker
, p. 1213 - 1217 (2007/10/02)
The oxidation of secondary amines to imines by iodosobenzene or catalysed by either manganese(III) or iron(III) porphyrins, or by a manganese(III) salen complex with iodosobenzene as the oxygen donor has been investigated.Both aromatic and aliphatic amines can be oxidized smoothly to the corresponding imines with iodosobenzene as the oxidant and the elimination of hydrogen takes place towards the least substituted carbon.Manganese(III) and iron(III) porphyrins and manganese(III) salen are found to catalyse the oxidation of secondary amines to imines with iodosobenzene as the terminal oxidant.Those amines that are less reactive when iodosobenzene is the oxidant, can be converted to the imines in higher yields if a catalyst is added, compared with the uncatalysed reaction.By-products such as carbonyls and nitrones are found in some of these reactions.The manganese(III) salen complex is found to be the best catalyst, followed by manganese(III) porphyrin and iron(III) porphyrin.On the basis of Hammett plots, isotopic labelling studies and other experimental investigations the mechanisms for the uncatalysed and catalysed amine-to-imine oxidations are discussed.
Process for synthesis of E-2-methyl-α,β-unsaturated aldehydes
-
, (2008/06/13)
A process is described for the synthesis of E-2-methyl-α,β-unsaturated aldehydes, which are useful as intermediates in the synthesis of the macrolide structure of the immunosuppressant FK-506. These compounds are also useful as ultraviolet radiation absor
ETUDE COMPARATIVE DE LA PHOTOREACTIVITE D'ENAMIDES ET DE THIOENAMIDS AROMATIQUES TERTIAIRES
Couture, A.,Dubiez, R.,Lablanche-Combier, A.
, p. 1835 - 1844 (2007/10/02)
Photolytic reactions of some simple aromatic enamides and thioenamides illustrate a novel example of the dramatic difference in the photochemical behaviour of carbonyl and thiocarbonyl compounds.In contrast with their oxo-analogues which are photoconverted into enaminoketones, thioenamides undergo photochemical cyclization to yield isoquinolinethione derivatives which can be easily convered into isoquinolones and tetrahydroisoquinolines.
