22273-79-6Relevant academic research and scientific papers
Enantioselective Intramolecular C?H Insertion of Donor and Donor/Donor Carbenes by a Nondiazo Approach
Zhu, Dong,Ma, Jun,Luo, Kui,Fu, Hongguang,Zhang, Li,Zhu, Shifa
, p. 8452 - 8456 (2016/07/19)
The first enantioselective intramolecular C?H insertion and cyclopropanation reactions of donor- and donor/donor-carbenes by a nondiazo approach are reported. The reactions were conducted in a one-pot manner without slow addition and provided the desired
Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles
Karmakar, Rajdip,Yun, Sang Young,Chen, Jiajia,Xia, Yuanzhi,Lee, Daesung
supporting information, p. 6582 - 6586 (2015/06/02)
The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.
An efficient stereoselective total synthesis of 11β-methoxycurvularin
Yadav,Vani, C. Divya,Bhasker,Reddy, B.V. Subba
, p. 291 - 300 (2014/10/15)
A very short and efficient stereoselective total synthesis of a macrocyclic ketone, 11β-methoxycurvularin was achieved by employing the Sharpless asymmetric epoxidation, formation of propargyl alcohols from an epoxy-chloride, and intramolecular Friedel-Cr
The stereochemical course of tricho-acorenol biosynthesis
Citron, Christian A.,Dickschat, Jeroen S.
supporting information, p. 7447 - 7450 (2013/11/06)
The biosynthesis of tricho-acorenol in Trichoderma harzianum was investigated by feeding stereospecifically deuterated mevalonolactone isotopomers, followed by a detailed GC/MS analysis of the incorporation of labelling. The results establish a highly ste
A carborane-derivative "click" reaction under heterogeneous conditions for the synthesis of a promising lipophilic MRI/GdBNCT agent
Toppino, Antonio,Bova, Maria Elena,Crich, Simonetta Geninatti,Alberti, Diego,Diana, Eliano,Barge, Alessandro,Aime, Silvio,Venturello, Paolo,Deagostino, Annamaria
, p. 721 - 728 (2013/02/23)
In this study, the Huisgen reaction has been used to functionalise a carborane cage with a lipophilic moiety and a 1,4,7,10-tetraazacyclododecane-1, 4,7,10-tetraacetic acid (DOTA) ligand to obtain a new Gd boron neutron-capture therapy (BNCT)/magnetic res
Efficient control for the cationic platinum(II)-catalyzed concise synthesis of two types of fused carbocycles with angular oxygen functionality
Kusama, Hiroyuki,Watanabe, Eiichi,Ishida, Kento,Iwasawa, Nobuharu
supporting information; experimental part, p. 2273 - 2277 (2012/06/30)
Double trouble: An efficient method for the preparation of two types of synthetically useful bicyclo[5.4.0]undecanes with an angular oxygen functionality was realized starting from easily available substrates; this method was based on the [3+2] cycloaddit
Synthesis of Gd(III)-C-palmitamidomethyl-C′-DOTAMA-C 6-o-carborane: A new dual agent for innovative MRI/BNCT applications
Aime, Silvio,Barge, Alessandro,Crivello, Antonella,Deagostino, Annamaria,Gobetto, Roberto,Nervi, Carlo,Prandi, Cristina,Toppino, Antonio,Venturello, Paolo
scheme or table, p. 4460 - 4466 (2009/02/07)
C-(2-Benzyloxy)-ethyl-C′-N-tert-butoxycarbonyl-aminomethyl-o- carborane (8), a potentially useful intermediate for BNCT, has been synthesised. This intermediate can be readily functionalised with several biological vectors and MRI contrast agents. In this
Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from N-(pent-2-en-4-ynyl)-β-lactams
Peng, Yu,Yu, Meng,Zhang, Liming
supporting information; experimental part, p. 5187 - 5190 (2009/06/06)
(Chemical Equation Presented) Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)- β-lactams is developed. In this reaction, a 5-exo-dig cyclization of the β-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.
Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion
Schomaker, Jennifer M.,Bhattacharjee, Somnath,Yan, Jun,Borhan, Babak
, p. 1996 - 2003 (2007/10/03)
An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.
Primary and secondary allyltitanium(IV) reagents in aldehyde allylation II: Application to an enantioselective preparation of a C1-C7 fragment of spiramycin
Razon, Patrick,N'Zoutani, Marie-Ange,Dhulut, Sylvie,Bezzenine-Lafollee, Sophie,Pancrazi, Ange,Ardisson, Janick
, p. 109 - 121 (2007/10/03)
A synthetic approach to the eastern part of spiramycin, an important antibiotic compound, is described. Introduction of the side chain was first envisaged through a Hoppe aldehyde allylation. This reaction was carried out between an optically pure aldehyde 32 and a (±)-γ-alkoxy allyltitanium(IV) species derived from a primary γ-alkoxy allyl (diisopropyl)carbamate. Under kinetic resolution conditions, the anti-Cram compound 35 was obtained in an 80:20 mixture, with the Cram isomer 34, in 81% yield. Employing the optically pure (S)-γ-alkoxy allyl (diisopropyl)carbamate 36, the corresponding (R)-γ-alkoxy allyltitanium (R)-'Ti'-III was generated under n-BuLi·TMEDA/Ti(Oi-Pr)4 conditions, that reacted with aldehyde 32 in double stereodifferentiation to deliver the expected Cram compound 40 in 80% yield (95% de). This latter corresponded to the C1-C7 fragment of spiramycin.
