Online citations, reference lists, and bibliographies.
← Back to Search

High 1,3-trans Stereoselectivity In Nucleophilic Substitution At The Anomeric Position And β-fragmentation Of The Primary Alkoxyl Radical In 3-amino-3-deoxy-ribofuranose Derivatives: Application To The Synthesis Of 2-epi-(-)-jaspine B.

Alma Sánchez-Eleuterio, L. Quintero, Fernando Sartillo-Piscil
Published 2011 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
The high inverse stereoselectivity in the nucleophilic substitution at the anomeric position of 3-amino-3-deoxy-ribofuranose derivatives is reported. This unprecedented stereoselectivity is explained in terms of preferential nucleophilic attack on the "inside face" of the respective five-membered ring oxocarbenium ion that orients pseudoequatorially to the benzylamine group placed at the C-3 position. In addition, an unusual β-fragmentation of a primary alkoxyl radical generated from its corresponding N-phthalimide derivative was achieved, and thus taking advantages of both reactions, the total synthesis of 2-epi-(-)-jaspine B was completed.
This paper references
10.1055/S-1990-20979
A Highly Diastereoselective Route to Disubstituted Tetrahydrofuran Derivatives by Substitution of γ-Lactols with Silylated Nucleophiles
A. Schmitt (1990)
10.1016/S0957-4166(00)80408-5
Synthetic routes to 2,5-disubstituted tetrahydrofurans
J.‐C. Harmange (1993)
10.1021/JO9708497
New Electronic Analogs of the Sialyl Cation: N-Functionalized 4-Acetamido-2,4-dihydroxypiperidines. Inhibition of Bacterial Sialidases.
I. Parr (1997)
10.1021/JA001179G
Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts
Steven B. Garber (2000)
10.1016/j.bmc.2008.11.026
Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.
D. Canals (2009)
10.1021/JA0214882
A general model for selectivity in olefin cross metathesis.
A. Chatterjee (2003)
10.1016/J.TETLET.2004.07.093
Communiols A-D: new mono- and bis-tetrahydrofuran derivatives from the coprophilous fungus Podospora communis
Y. Che (2004)
10.1021/JA0375176
Nucleophilic additions to fused bicyclic five-membered ring oxocarbenium ions: evidence for preferential attack on the inside face.
D. M. Smith (2003)
10.1016/J.TETLET.2003.12.003
Synthesis of alkaloids from aminol derivatives by β-fragmentation of primary alkoxyl radicals
A. Boto (2004)
10.1021/JO0709551
Beneficial effect of internal hydrogen bonding interactions on the beta-fragmentation of primary alkoxyl radicals. Two-step conversion of D-xylo- and D-ribofuranoses into L-threose and D-erythrose, respectively.
L. Hernandez-García (2007)
10.1016/S0040-4020(98)00405-0
RECENT ADVANCES IN STEREOSELECTIVE C-GLYCOSIDE SYNTHESIS
Y. Du (1998)
10.1021/NP010659Y
Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.
I. Kuroda (2002)
10.1002/CBER.19951280904
Stereoselective Substitution at Phenyl‐Substituted γ‐Lactols with Organometallic Compounds
A. Schmitt (1995)
10.1021/OL0492647
Using stereoelectronic effects to explain selective reactions of 4-substituted five-membered ring oxocarbenium ions.
D. M. Smith (2004)
10.1002/1099-0690(200012)2000:23<3893::AID-EJOC3893>3.0.CO;2-E
On the Stereoselectivity of γ‐Lactol Substitutions with Allyl‐ and Propargylsilanes − Synthesis of Disubstituted Tetrahydrofuran Derivatives
A. Schmitt (2000)
10.1039/B500186M
Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.
A. Bermejo (2005)
10.1016/J.TET.2008.10.087
Inverse stereoselectivity in the nucleophilic attack on five-membered ring oxocarbenium ions. Application to the total synthesis of 7-epi-(+)-goniofufurone
L. Hernandez-Garcia (2009)
10.1016/S0040-4039(02)00123-5
Synthesis of α,ω-differently substituted cyclic ethers from carbohydrates by β-fragmentation of alkoxyl radicals
A. Boto (2002)
10.1016/S0008-6215(00)84266-4
Acyloxy neighboring-group participation in the acid-catalyzed cleavage of methyl 2,3-anhydro-beta-D-ribofuranoside.
D. Hollenberg (1975)
10.1021/JA972599H
Probing the Specificity of Aminoglycoside−Ribosomal RNA Interactions with Designed Synthetic Analogs
P. Alper (1998)
10.1021/JA042668+
Regarding the mechanism of olefin metathesis with sol-gel-supported Ru-based complexes bearing a bidentate carbene ligand. Spectroscopic evidence for return of the propagating Ru carbene.
Jason S. Kingsbury (2005)
10.1021/np800481w
Tetrahydrofuran acetogenins from Laurencia glandulifera.
Maria Kladi (2009)
10.1021/NP050283E
Bioactive tetrahydrofuran lignans from Peperomia dindygulensis.
Jian-Lin Wu (2005)
10.2174/157017806778341889
Letters in Organic Chemistry [Rapid Access to Enantiomerically Pure 3,6-Anhydro-2-deoxy-7-phenylglyconolactones. Synthesis of Diastereoisomers of (+)-Goniofufurone]
L. Quintero (2006)
10.1021/JA0524043
Stereoselective C-glycosylation reactions of ribose derivatives: electronic effects of five-membered ring oxocarbenium ions.
Catharine H. Larsen (2005)
10.1039/B600056H
Electrostatic interactions in cations and their importance in biology and chemistry.
D. M. Smith (2006)
10.1021/JO7017729
Rhodium-catalyzed decarbonylation of aldoses.
R. Monrad (2007)
10.1002/EJOC.200600720
Synthesis of Alkaloid Analogues from β‐Amino Alcohols by β‐Fragmentation of Primary Alkoxyl Radicals
A. Boto (2007)
10.1002/ANIE.200601963
Gold(I)-catalyzed bis-spiroketalization: synthesis of the trioxadispiroketal-containing A-D rings of azaspiracid.
Y. Li (2007)
10.1021/AR000114F
The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.
T. M. Trnka (2001)
10.1021/OL0473290
Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B).
Pushpal Bhaket (2005)
10.1055/S-1998-1711
Facile Generation of Alkoxy Radicals from N-Alkoxyphthalimides
S. Kim (1998)
10.1021/AR00059A002
Ring-Closing Metathesis and Related Processes in Organic Synthesis
R. Grubbs (1995)
10.1021/JO034442F
β-Fragmentation of Primary Alkoxyl Radicals versus Hydrogen Abstraction: Synthesis of Polyols and α,ω-Differently Substituted Cyclic Ethers from Carbohydrates
A. Boto (2003)
10.1021/jo1005284
Stereoselective divergent synthesis of four diastereomers of pachastrissamine (jaspine B).
Yuji Yoshimitsu (2010)
10.1021/JA993349Z
A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions
Catharine H. Larsen (1999)
10.1016/J.TETASY.2008.04.017
Jaspine B (pachastrissamine) and 2-epi-jaspine B: synthesis and structural assignment
E. Abraham (2008)
10.1016/J.CARRES.2006.10.015
Nucleophilic substitution at the anomeric position of 1,2-O-isopropylidenefuranose derivatives. A novel stereoselective synthesis of cyclic phosphates analogous to cAMP.
M. Romero (2006)
10.1002/9783527619481
Handbook of metathesis
R. Grubbs (2003)



This paper is referenced by
10.1016/J.TET.2012.12.049
Sugar-based monodentate phosphoramidite ligands for Cu-catalyzed enantioselective conjugate addition to enones
T. Bauer (2013)
10.1016/J.TETASY.2013.07.003
Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity
P. Ghosal (2013)
10.1002/JCCS.201100744
Synthesis of a Furanosyl‐pyranone Derivative Related to the Tri‐O‐heterocyclic Core of Herbicidins
Ching-Yun Hsu (2012)
10.1021/acs.joc.7b01211
Stereocontrolled Nucleophilic Addition to Five-Membered Oxocarbenium Ions Directed by the Protecting Groups. Application to the Total Synthesis of (+)-Varitriol and of Two Diastereoisomers Thereof.
Alma Sánchez-Eleuterio (2017)
10.1021/jo502757c
Total synthesis of cephalosporolide E via a tandem radical/polar crossover reaction. The use of the radical cations under nonoxidative conditions in total synthesis.
Omar Cortezano-Arellano (2015)
10.1016/J.TETLET.2011.09.045
A five-step formal synthesis of (−)-Jaspine B
Silvano Cruz-Gregorio (2011)
10.3762/bjoc.9.291
Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block
Volker M Schmiedel (2013)
10.1002/9781119295266.CH7
Protecting‐Group‐Free Synthesis in Carbohydrate Chemistry
A. Cordero-Vargas (2018)
10.1016/J.TETASY.2012.04.009
Total synthesis of the acetyl derivatives of lyxo-(2R,3R,4R)-phytosphingosine and (−)-jaspine B
G. Rao (2012)
10.1002/chem.201406258
Concerning the deactivation of cobalt(III)-based porphyrin and salen catalysts in epoxide/CO2 copolymerization.
W. Xia (2015)
10.1016/j.carres.2016.01.009
Marine cytotoxic jaspine B and its stereoisomers: biological activity and syntheses.
M. Martinková (2016)
10.1016/J.TETLET.2015.08.003
Total synthesis of the proposed structure of decurrenside D
Verónica González-Márquez (2015)
10.1016/J.TETASY.2014.04.002
Total synthesis of (−)-jaspine B and its 4-epi-analogue from d-xylose
M. Martinková (2014)
10.1016/j.carres.2016.01.011
Total synthesis and antiproliferative/cytotoxic profiling of 2-epi-jaspine B.
E. Mezeiová (2016)
10.1016/J.TETLET.2018.12.058
Blue light photoredox decarboxylation and tin-free Barton-McCombie reactions in the stereoselective synthesis of (+)-muscarine
Victoria Rodríguez-Tzompanzi (2019)
10.1002/EJOC.201801245
Regioselective Ring Opening of 1,3‐Dioxane‐Type Acetals in Carbohydrates
Jonas Janssens (2018)
10.1016/J.TETLET.2011.08.170
A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl D-lyxo-phytosphingosine
G. Rao (2011)
10.1016/J.TETLET.2011.07.032
A common and stereoselective strategy for the synthesis of N,O,O,O-tetra-acetyl d-ribo-(2S,3S,4R)-phytosphingosine and 2-epi-jaspine B
G. Rao (2011)
10.1016/J.TET.2013.03.091
Synthesis of pachastrissamine (jaspine B) and its derivatives by the late-stage introduction of the C-2 alkyl side-chains using olefin cross metathesis
Yuji Yoshimitsu (2013)
10.1016/J.TET.2013.07.028
A common approach to the total synthesis of l-arabino-, l-ribo-C18-phytosphingosines, ent-2-epi-jaspine B and 3-epi-jaspine B from d-mannose
M. Martinková (2013)
10.1016/j.carres.2014.11.004
Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation.
M. Martinková (2015)
10.1021/acs.chemrev.7b00234
Recent Advances in the Chemical Synthesis of C-Glycosides.
You Yang (2017)
10.1016/j.carres.2012.01.013
An efficient and convenient formal synthesis of Jaspine B from D-xylose.
Ming-Li Zhao (2012)
10.1016/J.TET.2013.06.091
Rapid access to jaspine B and its enantiomer
C. Santos (2013)
10.1021/jo301153u
Intramolecular 1,8-hydrogen atom transfer reactions in disaccharide systems containing furanose units.
S. Guyenne (2012)
Semantic Scholar Logo Some data provided by SemanticScholar