63922-69-0Relevant articles and documents
The stereoselective synthesis of conjugated allylsilanes
Mahran, Mohamed Refat H.,Yosef, Hisham Abdallah A.,Effenberger, Franz
, p. 2283 - 2295 (2006)
2-trimethylsilylethylidenetriphenylphosphorane (5) (Seyferth-Wittig reagent) reacts stereoselectively with the carbonyl compounds 6a-f to give the conjugated allylsilanes 7a-f, each as a mixture of E-and Z-isomers. The stereoselectivity of reactions of E-
Total synthesis of leucosceptroids a and B
Guo, Sheng,Liu, Jie,Ma, Dawei
, p. 1298 - 1301 (2015)
Leucosceptroids A and B are sesterterpenoids with potent antifeedant and antifungal activities. A more efficient gram-scale total synthesis of leucosceptroid B and the first total synthesis of leucosceptroid A are presented. The key transformations include an aldol reaction between a substituted dihydrofuranone and an (S)-citronellal-derived aldehyde, a SmI2-mediated intramolecular ketyl-olefin radical cyclization, and final-stage alcohol oxidation.
Catalytic cyclometallation in steroid chemistry IV: Efficient method for the synthesis of tetrahydrothiophene, tetrahydroselenophen and cyclopentanone derivatives of (5α)-cholestane
D'Yakonov, Vladimir A.,Tuktarova, Regina A.,Islamov, Ilgiz I.,Khalilov, Leonard M.,Dzhemilev, Usein M.
, p. 77 - 84 (2016)
Catalytic cycloalumination of (3β,5α)-3-vinylcholestane and (3α,5α)-3-allylcholestane with Et3Al catalyzed by Cp2ZrCl2 was performed for the first time to give previously unknown aluminacyclopentanes in ～90% yield; these p
Evaluation of transition-state mimics in a superior BACE1 cleavage sequence as peptide-mimetic BACE1 inhibitors
Hattori, Yasunao,Kobayashi, Kazuya,Deguchi, Ayaka,Nohara, Yukie,Akiyama, Tomomi,Teruya, Kenta,Sanjoh, Akira,Nakagawa, Atsushi,Yamashita, Eiki,Akaji, Kenichi
, p. 5626 - 5640 (2015/11/11)
A superior substrate sequence for BACE1 containing transition-state mimics at the scissile site was evaluated as a protease inhibitor. Hydroxymethylcarbonyl (HMC) and hydroxyethylamine (HEA) isosteres were selected as the transition state mimics, and inco
Anodic coupling reactions: Exploring the generality of Curtin-Hammett controlled reactions
Redden, Alison,Moeller, Kevin D.
supporting information; experimental part, p. 1678 - 1681 (2011/05/04)
Intramolecular anodic olefin coupling reactions can be compatible with the presence of dithioketal protecting groups even though the dithioketal oxidizes at a lower potential than either of the groups participating in the cyclization. In such cases, product formation is controlled by the Curtin-Hammett Principle. In this study, the generality of such reactions is examined along with the use of alternative reaction conditions to suppress unwanted side reactions.
Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine
Belanger, Guillaume,Larouche-Gauthier, Robin,Menard, Frederic,Nantel, Miguel,Barabe, Francis
, p. 704 - 712 (2007/10/03)
Vilsmeier-Haack type cyclizations proved to be particularly efficient for generating parts of the polycyclic cores of many alkaloids, although only monocyclizations have so far been reported. With the goal of rapidly and efficiently constructing polycycli
Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yI]-cyclohexanecarbaldehyde with Loss of Formyl Carbon
Kuroda, Chiaki,Murase, Atsushi,Suzuki, Hideyuki,Endo, Toru,Anzai, Shuzo
, p. 1639 - 1647 (2007/10/03)
Treatment of cis- and trans-4-[3-(trimethylsilyl)prop-1-en-1-yl]cydohexanecarbaldehyde (2a and 2b) with tetrabutylammonium fluoride in dilute tetrahydrofuran afforded 7-vinylbicyclo(2.2.1]heptan-1-ol (3), the same product obtained from 4-[3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanone (1). It was found that oxidative deformyhition of 2a, b to 1 takes place under basic conditions before the cyclization to 3. It was also shown that cyclization of allylsilane with carbonyl does not proceed via an eclipsed conformation.
Total Synthesis of (+/-)-Pyridoxatin
Snider, Barry B.,Lu, Qing
, p. 8065 - 8070 (2007/10/02)
An efficient two-step route to pyridoxatin analogues 13 and 15 has been developed.Condensation of 4-hydroxypyridone (4) with citronellal (10) affords o-quinone methide intermediate 11, which reacts further to give inverse electron demand Diels-Alder adducts 12 and 16 and ene adduct 14.Oxidation of 12 and 14 with MoO5 by Sammes' procedure completes the synthesis of 13 and 15.Using this approach, the first total synthesis of (+/-)-pyridoxatin (1) has been carried out in seven steps from cis-2,4-dimethylcyclohexanone (21).The key step is the condensation of 4-hydroxypyridone (4) with the allylic silane aldehyde 26 to give 35percent of cyclohexylpyridones 2 and 30.
Intramolecular anodic olefin coupling reactions: A useful method for carbon-carbon bond formation
Hudson, Christine M.,Marzabadi, Mohammad R.,Moeller, Kevin D.,New, Dallas G.
, p. 7372 - 7385 (2007/10/02)
The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The e
