Stereoselective Synthesis ofl-Oliose Trisaccharide via Iterative Alkynol Cycloisomerization and Acid-Catalyzed Glycosylation†

2002 ◽  
Vol 4 (22) ◽  
pp. 3979-3981 ◽  
Author(s):  
Frank E. McDonald ◽  
Minglang Wu
Keyword(s):  
Stereoselective Synthesis ◽  
Acid Catalyzed

Stereoselective Synthesis of C-Ketosides by Lewis Acid Catalyzed C-Glycosylation of Alkynyl-Ketoses.

ChemInform ◽  
2003 ◽  
Vol 34 (14) ◽  
Author(s):  
Ana M. Gomez ◽  
Clara Uriel ◽  
Serafin Valverde ◽  
Slawomir Jarosz ◽  
J. Cristobal Lopez
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Acid Catalyzed

Counterion effects in the catalytic stereoselective synthesis of 2,3′-pyrrolidinyl spirooxindoles

2014 ◽  
Vol 50 (40) ◽  
pp. 5242-5244 ◽  
Author(s):  
Jacob P. MacDonald ◽  
Benjamin H. Shupe ◽  
John D. Schreiber ◽  
Annaliese K. Franz
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Acid Catalyzed

A Lewis acid-catalyzed stereoselective [3+2] annulation of crotylsilanes with iminooxindoles is reported to access 2,3′-pyrrolidinyl spirooxindoles with four stereocenters.

Intercepting the Nazarov Oxyallyl Intermediate with α-Formyl­vinyl Anion Equivalents to Access Formal Morita–Baylis–Hillman Alkylation Products

Synlett ◽  
2017 ◽  
Vol 28 (12) ◽  
pp. 1486-1490 ◽  
Author(s):  
F. West ◽  
Yen-Ku Wu ◽  
Rongrong Lin
Keyword(s):  
Lewis Acid ◽  
Stereoselective Synthesis ◽  
Domino Reaction ◽  
Alkylation Process ◽  
Acid Catalyzed

A Lewis acid catalyzed cationic domino reaction involving sequential electrocyclization and polar addition of allenol ethers onto the resulting oxyallyl species is described. The overall sequence allows a highly stereoselective synthesis of densely substituted cyclopentanoid compounds containing α-formylvinyl functionality which is formally equivalent to products of a Morita–Baylis–Hillman alkylation process.

Versatile use of acid-catalyzed ring-opening of β-aziridinyl-α,β-enoates to stereoselective synthesis of peptidomimetics

Tetrahedron ◽  
2007 ◽  
Vol 63 (37) ◽  
pp. 9243-9254 ◽  
Author(s):  
Hirokazu Tamamura ◽  
Tomohiro Tanaka ◽  
Hiroshi Tsutsumi ◽  
Koji Nemoto ◽  
Satoko Mizokami ◽  
...  
Keyword(s):  
Ring Opening ◽  
Stereoselective Synthesis ◽  
Acid Catalyzed

(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides

2009 ◽  
Vol 19 (11) ◽  
pp. 3093-3095 ◽  
Author(s):  
Bala Kishan Gorityala ◽  
Shuting Cai ◽  
Jimei Ma ◽  
Xue-Wei Liu
Keyword(s):  
Stereoselective Synthesis ◽  
Camphorsulfonic Acid ◽  
Acid Catalyzed

A stereoselective synthesis of digitoxin. On cardioactive steroids. XIII

1984 ◽  
Vol 62 (7) ◽  
pp. 1403-1405 ◽  
Author(s):  
Thomas Y. R. Tsai ◽  
Haolun Jin ◽  
Karel Wiesner
Keyword(s):  
Stereoselective Synthesis ◽  
New Method ◽  
Cardioactive Steroids ◽  
Acid Catalyzed

The first highly stereoselective synthesis of digitoxin is described. The furyl derivative of digitoxigenin was coupled with one unit of digitoxose using our previously described acid catalyzed method. For the second and third glycosylation a new method involving ethyl thioglycosides and 1,3-participation by a p-methoxy benzoate group was developed. As the final step after deprotection of the triglycoside, the 17-furyl group in the steroid aglycone was converted to a butenolide by our oxidative method.

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