106929-09-3Relevant academic research and scientific papers
Palladium(II)-catalyzed cyclization of urethanes and its application to a total synthesis of 1-deoxynojirimycin
Yokoyama, Hajime,Kobayashi, Hisatake,Miyazawa, Masahiro,Yamaguchi, Seiji,Hirai, Yoshiro
, p. 283 - 292 (2008/09/17)
We have employed a palladium(II)-catalyzed cyclization of allylic alcohol as a key reaction to achieve a total synthesis of the azasugar 1-deoxynojirimycin from o-mannitol. This reaction should be useful for the stereoselective construction of natural poly-substituted piperidine derivatives.
Stereoselective total synthesis of (+)-goniothalesdiol and (+)-2,5-epi-goniothalesdiol from D-mannitol
Ghosh, Subhash,Rao, Chapala Nageswara,Dutta, Samit Kumar
, p. 1464 - 1466 (2008/03/11)
An efficient and practical total synthesis of (+)-goniothalesdiol and its 2,5-epi analogue is described herein. The key features include a diastereoselective reduction of C-5 keto with Zn(BH4)2 to generate the desired stereochemistry
An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol: Total synthesis of (-)-muricatacin
Chandrasekhar,Chandra, Kusum L,Singh, Vinod K
, p. 2773 - 2775 (2007/10/03)
A general approach towards the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol has been described. The approach has successfully been used for the total synthesis of (-)-muricatacin, an anti-tumor natural product.
Total synthesis of (-)- and (+)-lentiginosine
Chandra, Kusum L.,Chandrasekhar,Singh, Vinod K.
, p. 4630 - 4633 (2007/10/03)
Total synthesis of (-)-lentiginosine was achieved from D-mannitol using highly stereoselective reactions. Similarly, (+)-lentiginosine was synthesized from L-tartaric acid.
Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.
Yokoyama,Otaya,Kobayashi,Miyazawa,Yamaguchi,Hirai
, p. 2427 - 2429 (2007/10/03)
The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.
Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization
Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 165 - 190 (2007/10/03)
Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.
Preparation of 2,5-anhydrohexitols (part II). Intramolecular nucleophilic substitution of cyclic sulfates
Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 191 - 207 (2007/10/03)
The 2-O-acetyl-3,4-di-O-benzyl-5,6-O-cyclic sulfates 5, 16 and 25, derived from D-arabinose, D-ribose and D-xylose, respectively, are useful precursors in the synthesis of 2,5-anhydrohexitols. 5-Exo-tet cyclization of compounds 5, 16, and 25 under the inf
Postcondensation modifications of Ugi four-component condensation products: 1-Isocyanocyclohexene as a convertible isocyanide. Mechanism of conversion, synthesis of diverse structures, and demonstration of resin capture
Keating,Armstrong
, p. 2574 - 2583 (2007/10/03)
The concept of a 'universal isocyanide' that enables postcondensation modification of Ugi four-component condensation products is introduced. This strategy is suited for the synthesis of libraries. By using 1-isocyanocyclohexene as the isocyanide input in the Ugi reaction, the product cyclohexenamides can be converted to a variety of products. From the original α-(acylamino) amides, new carboxylic acids, esters, and thioesters are produced from acid-activated conversion of the cyclohexenamide moiety. It has been determined that the intermediate in conversion of this type is an oxazolinium-5-one (munchnone) that reacts with many nucleophiles to yield the products above. The munchnone can also undergo cycloaddition with acetylenic dipolarophiles to form pyrroles. Through internal nucleophilic attack, Ugi products are shown to convert to a protected monosaccharide derivative and to 1,4-benzodiazepine-2,5-diones. All of the conversions described consist of a single step. Resin capture of Ugi products is demonstrated, in which a solution condensation reaction is followed by trapping of the products onto solid support resin. Both the trapping step and subsequent cleavage of products from the resin occur in very high yield.
Construction of all O-alkoxy D-tetrose and D-pentose stereoisomers from 2,3-O-isopropylidene-D-glyceraldehyde using 2-(trimethylsilyl)thiazole as a formyl anion equivalent
Dondoni,Orduna,Merino
, p. 201 - 210 (2007/10/02)
All D-tetroses and D-pentoses having differentially protected hydroxy groups are synthesized by an iterative one-carbon chain-elongation cycle commencing with the addition of 2-(trimethylsilyl)thiazole to 2,3-O-isopropylidene-D-glyceraldehyde. One half of
Preferred Conformation of C-Glycosides. 8. Synthesis of 1,4-Linked Carbon Disaccharides
Wang, Yuan,Babirad, Stefan A.,Kishi, Yoshito
, p. 468 - 481 (2007/10/02)
Three general synthetic routes to 1,4-linked carbon disaccharides (e.g., 3, 4, 15-17, 21-23, 44, and 45) are presented.Control of the stereochemistry at C.1', C.2', C.5'and C.4, the incorporation of deuterium labels at the C.α position, and structural mod
