78148-00-2Relevant academic research and scientific papers
A unified and common intermediate strategy for the asymmetric total synthesis of 3-deoxy-neo-inositol and conduritol E
Panda, Amarendra,Biswas, Rayhan Gafur,Pal, Shantanu
supporting information, p. 3625 - 3628 (2016/07/19)
A competent, simplistic, and unified synthetic approach has been outlined for enantiomerically pure 3-deoxy-neo-inositol and conduritol E starting from D-ribose via a common chiral cyclohexenol derivative. The focal attributes of the synthetic route inclu
Total synthesis of quercitols: (+)- allo -, (-)- proto -, (+)- talo -, (-)- gala -, (+)- gala -, neo -, and (-)- epi -quercitol
Aucktor, Johannes,Brückner, Reinhard
, p. 250 - 258 (2015/03/05)
The cyclohexenenones exo- and endo-2 were converted into the cyclohexenyl acetates exo- and endo-3 and exo- and endo-5 with a diastereoselectivity of >99:1 (2 steps). Ether cleavage with DDQ in CH2Cl2/H2O (20:1) and in situ ketal hydrolysis afforded the cyclohexenones 6 and 7 in up to 83% and 87% yield, respectively. Compound 6 was converted into (+)-allo- and (-)-proto-quercitol with a diastereoselectivity of 100:0 (4 steps). Moreover, 6 was carried on to (-)-talo-quercitol whereas 7 furnished the four remaining title quercitols (3-5 steps) including both enantiomers of gala-quercitol.
Stereoselective syntheses of racemic quercitols and bromoquercitols starting from cyclohexa-1,4-diene: Gala-, epi-, muco-, and neo-quercitol
Aydin, G?kay,Savran, Tahir,Akta?, Fatih,Baran, Arif,Balci, Metin
, p. 1511 - 1524 (2013/05/21)
The efficient synthesis of gala-, epi-, neo-, and muco-quercitols and some brominated quercitols starting from cyclohexa-1,4-diene is reported. Treatment of the dibromide, obtained by the addition of bromine to cyclohexa-1,4-diene, with m-chloroperbenzoic
An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene
Baran, Arif,Secen, Hasan,Balci, Metin
, p. 1500 - 1502 (2007/10/03)
gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aα,5α,7aα)-5-metho
Asymmetric synthesis of (+)-allo-quercitol and (+)-talo-quercitol via free radical cycloisomerization of an enantiomerically pure alkyne-tethered aldehyde derived from a carbohydrate
Yadav,Maiti,Sankar,Kunwar
, p. 8370 - 8378 (2007/10/03)
We describe for the first time the free radical cyclization of enantiomerically pure alkyne-tethered aldehydes obtained from a carbohydrate (6, 7). The synthesis of compounds 6 and 7 obtained from a derivative of D-ribose is reported. These radical precursors have been submitted to cyclization with tributyltin hydride plus azobisisobutyronitrile to yield, after ring closure, two carbocycles, respectively. These carbocycles have been obtained as mixtures of E and Z vinyltin isomers, but with excellent diastereoselection at the new stereocenter formed during the ring closure. After protodestannylation, only one diastereomer was detected and isolated. The absolute configuration at the new stereocenter formed during the carbocyclization has been established by detailed 1H NMR analysis. The specific transformation of 7-methoxymethoxy-2,2-dimethyl-4-methylene-5-tertbutyldimethylsilyloxy- (3aR,5S,7S,7aS)-perhydrobenzo[d] [1,3]dioxole into optically pure (+)-allo-quercitol and (+)-talo-quercitol is described. From these results, we conclude that under an appropriate choice of radical precursors and conditions, the synthesis of highly functionalized cyclohexane derivatives of biological interest is now available.
Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis
Hyldtoft, Lene,Madsen, Robert
, p. 8444 - 8452 (2007/10/03)
A general method for carbocyclization of carbohydrates is described using two consecutive organometallic transformations: a novel zinc-mediated domino reaction to give functionalized dienes followed by ring-closing olefin metathesis. In the first reaction
Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
Angelaud, Remy,Babot, Odile,Charvat, Trevor,Landais, Yannick
, p. 9613 - 9624 (2007/10/03)
Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
An Advantageous Synthesis of 1D- and 1L-1,2,3,5/4-Cyclohexanepentol
Biamonte, Marco A.,Vasella, Andrea
, p. 688 - 694 (2007/10/03)
The title compounds D-10 and L-10 were prepared from 1 in eight steps and in a combined overall yield of 41-49%.
A novel synthesis of DL-proto-, and DL-vibo- quercitol via 1,4- cyclohexadiene
Salamci, Emine,Secen, Hasan,Suetbeyaz, Yasar,Balci, Metin
, p. 2223 - 2234 (2007/10/03)
Photooxygenation of 1,4-cyclohexadiene 3 followed by reduction with LiAIH4 or thiourea gave (25/1)-cyclohex-3-ene-triol 7a. trans-Hydroxylation of triol 7a with three different methods afforded both of proto-quercitol 1a and vibo-quercitol 2a.
