76358-53-7Relevant academic research and scientific papers
Non-Cp titanium alkoxide-based homolytic ring-opening of epoxides by an intramolecular hydrogen abstraction in β-titanoxy radical intermediates
Kawaji, Tsuyoshi,Shohji, Noriaki,Miyashita, Kenji,Okamoto, Sentaro
, p. 7857 - 7859 (2011/09/15)
A low-valent titanium species derived in situ from Ti(O-i-Pr)4, Me3SiCl and Mg powder in tetrahydrofuran reacted with epoxides to selectively provide less hindered alcohols via a homolytic ring-opening of epoxides, in which the intermediate β-titanoxy radical intramolecularly abstracted a hydrogen atom from an alkoxy moiety in the titanium complexes.
Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans
Hanessian, Stephen,Szychowski, Janek,Pablo Maianti
supporting information; experimental part, p. 429 - 432 (2009/09/25)
(Chemical Equation Presented) A synthesis of verdamicin C2 and its congener C2a has been accomplished from sisomicin relying on a novel oxidative transformation of an allylic azide to the corresponding α,β- unsaturated aldehyde, and its stereocontrolled elaboration into the intended 5′ side chain of verdamicin C2 and C2a. In vitro antibacterial testing shows that both C6′ epimers in verdamicin C2 and C2a are equally active against a variety of bacterial strains. Oxidation of allylic primary azides, ethers, and esters of 2-substituted dihydro[2H]pyrans with SeO2 leads directly to the corresponding aldehydes.
1,2-Disubstituted cyclohexane nucleosides: Comparative study for the synthesis of cis and trans adenosine analogues
Vi?a, Dolores,Santana, Lourdes,Uriarte, Eugenio,Terán, Carmen
, p. 473 - 478 (2007/10/03)
A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (±)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu cond
Syntheses of seven-membered rings: Ruthenium-catalyzed intramolecular [5+2] cycloadditions
Trost, Barry M.,Shen, Hong C.,Horne, Daniel B.,Toste, F. Dean,Steinmetz, Bernhard G.,Koradin, Christopher
, p. 2577 - 2590 (2007/10/03)
The Ru-catalyzed intramolecular [5+2] cycloaddition of cyclopropylenynes is investigated with respect to the regio- and diastereoselectivity as well as the functional group compatibility of the reaction. Evidence for the mechanism as occurring through a ruthenacyclopentene intermediate is elucidated from 1) the study of the diastereoselectivity of the cycloaddition; 2) the effect of variation of substituents on the regioselectivity of cyclopropyl bond cleavage in 1,2-trans- and 1,2-cis-disubstituted cyclopropanes and 3) examples that clearly do not involve ruthenacyclohexene as intermediates as products still incorporate the cyclo propyl moiety. The scope and limitations of the Ru-catalyzed cycloaddition are discussed and compared with the Rh-catalyzed reaction. The potential power of this methodology towards natural product total synthesis is demonstrated by the formation of several polycyclic systems with the chosen reaction conditions and readily available cyclopropylenyne substrates.
Synthesis of a C,D-Ring Fragment of Artemisinin
Avery, Mitchell A.,Jennings-White, Clive,Chong, Wesley K. M.
, p. 1789 - 1792 (2007/10/02)
A multistep preparation is described for carboxyvinylsilane 6, which upon reaction with ozone initially gave dioxetane 8 as a transient intermediate in a highly stereoselective manner. Subsequent rearrangement at ambient temperature resulted in cyclizatio
Silyl Halides from (Phenylseleno)silanes. Reaction with Oxiranes and Alcohols To Give Hydrolytically Stable Silyl Ethers.
Detty, Michael R.,Seidler, Mark D.
, p. 1283 - 1292 (2007/10/02)
The preparation of (phenylseleno)silanes and their reactions with halogens (Cl2, Br2, I2) to give silyl halides and diphenyl diselenide are described.Highly hindered tert-butyldimethyl and tert-butyl diphenylsilyl halides were easily prepared.The reaction of silyl bromides and iodides with oxiranes followed by diazabicyclononane treatment gave allylic alcohol silyl ethers.Tertiary alcohols reacted rapidly with silyliodides to give hydrolytically stable silyl ethers.Treatment of the silyl ethers with tetra-n-butylammonium fluoride gave the free alcohols withoutrearrangement or isomerization.
Electrophilic Conversion of Oxiranes to Allylic Alcohols with tert-Butyldimethylsilyl Iodide
Detty, Michael R.
, p. 924 - 926 (2007/10/02)
tert-Butyldimethylsilyl iodide (I) is prepared from the reaction of iodine with (phenylseleno)-tert-butyldimethylsilane in acetonitrile.The reaction of oxiranes with 1 followed by treatment with 1,5-diazabicyclonon-5-ene gives accetable yields of allylic alcohols isolated as their tert-butyldimethylsilyl ethers.Ring opening involves cleavage of the bond to the more highly substituted carbon.
