87770-83-0Relevant articles and documents
Synthesis of 1-(5,6-dihydro-2H-thiopyran-2-yl)uracil by a Pummerer-type thioglycosylation reaction: the regioselectivity of allylic substitution
Yoshimura, Yuichi,Yamazaki, Yoshiko,Saito, Yukako,Takahata, Hiroki
, p. 9091 - 9102 (2009)
1-(5,6-Dihydro-2H-thiopyran-2-yl)uracil derivatives, a new 4′-thio-D4-nucleoside analogue, were synthesized by reacting 5,6-dihydro-2H-thiopyran sulfoxide and persilylated uracil in a Pummerer-type thioglycosylation reaction. The reaction of 5-alkyl subst
A highly efficient synthesis of the FGH ring of micrandilactone A. application of thioureas as ligands in the co-catalyzed Pauson-Khand reaction and Pd-catalyzed carbonylative annulation
Tang, Yefeng,Zhang, Yandong,Dai, Mingji,Luo, Tuoping,Deng, Lujiang,Chen, Jiahua,Yang, Zhen
, p. 885 - 888 (2005)
(Chemical Equation Presented) The functionalized FGH ring system of micrandilactone A was successfully constructed in high selectivity and good yields. The key reactions in our strategy are the Co-thiourea-catalyzed stereoselective, intramolecular Pauson-
Synthesis of an allylic gem-difluoromethylene building block via radical-mediated difluorocyclopropane ring opening
Milne, Kirsty,Henry, Martyn C.,Jamieson, Craig
supporting information, (2021/09/16)
We report an optimised and highly efficient synthetic route towards a valuable functionalised fluorinated building block. The key-steps include difluorocyclopropanation of a disubstituted alkene with a suitable difluorocarbene precursor, and a radical-ind
Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives
Bitai, Jacqueline,Slawin, Alexandra M.Z.,Cordes, David B.,Smith, Andrew D.
supporting information, (2020/07/27)
The scope and limitations of a tandem N-allylation/[2,3]-rearrangement protocol are investigated through the incorporation of a variety of functional groups within an allylic phosphate precursor. This method uses readily accessible N,N-dimethylglycine aryl esters and functionalized allylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequent enantioselective [2,3]-sigmatropic rearrangement, promoted by the chiral isothiourea tetramisole, generates α-amino acid derivatives with two contiguous stereocenters. The incorporation of electron-withdrawing ester and amide groups gave the best results, furnishing the desired products in moderate to good yields (29-70percent), with low diastereocontrol (typically 60:40 dr) but high enantioselectivity (up to 90:10 er). These results indicate that substrate-catalyst interactions in the proposed transition state are sensitive to the substitution pattern of the substrates.
Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy
Schrank, Cassandra L.,Danneman, Michael W.,Prebihalo, Emily A.,Anderson, Robert E.,Gibson, Tyler J.,Wuest, William M.,Mullins, Richard J.
supporting information, (2020/04/27)
In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-N-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (?)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidinone auxiliary.
Stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol
Agostinelli, Sonia,De Angelis, Martina,Lucarini, Claudia,Primitivo, Ludovica,Ricelli, Alessandra,Righi, Giuliana,Sappino, Carla
, (2020/05/14)
The first stereocontrolled total synthesis of iminosugar 1,4-dideoxy-1,4-imino-D-iditol is described. The key step in our approach was the double diastereoselection in the asymmetric dihydroxylation (AD) of suitable optically active olefin, the chiral vin
Stereodivergent Hydroboration of Allenes
Nagashima, Yoshiyuki,Sasaki, Keiji,Suto, Takahiro,Sato, Takaaki,Chida, Noritaka
supporting information, p. 1024 - 1028 (2018/03/21)
Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.
Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles
Adamson, Nathan J.,Wilbur, Katherine C. E.,Malcolmson, Steven J.
supporting information, p. 2761 - 2764 (2018/03/06)
We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful chemical building blocks for downstream synthesis.
A short convergent synthesis of the [3.2.1]dioxabicyclooctane subunit of sorangicin A via regioselective epoxide opening
Raghavan, Sadagopan,Nyalata, Satyanarayana
, p. 1071 - 1077 (2018/02/10)
In this paper, we disclose the synthesis of the dioxabicyclo[3.2.1]octane subunit of the potent antibiotic sorangicin A. The synthesis was achieved in a convergent manner in 8 steps. Regio- and stereoselective intermolecular epoxide opening, ring-closing metathesis and iodo-etherification are key steps. cis-2-Butene diol has been employed as a common staring material.
Stereoselective synthesis of the C3-C15 fragment of callyspongiolide
Reddy Ramidi, Gopal,Yadav, Jhillu S.,Mohapatra, Debendra K.
supporting information, p. 3579 - 3582 (2018/09/10)
The synthesis of C3-C15 fragment of callyspongiolide, a 14-membered macrolides isolated from the marine sponge Callyspongia sp., which was collected from the Indonesia, is reported. Highlights of the synthesis include construction of E-olefin through Juli
