Synthesis of a Histamine H3Receptor Antagonist—Manipulation of Hydroxyproline Stereochemistry, Desymmetrization of Homopiperazine, and Nonextractive Sodium Triacetoxyborohydride Reaction Workup

2010 ◽  
Vol 75 (13) ◽  
pp. 4463-4471 ◽  
Author(s):  
Daniel J. Pippel ◽  
Lana K. Young ◽  
Michael A. Letavic ◽  
Kiev S. Ly ◽  
Bita Naderi ◽  
...  
2019 ◽  
Vol 23 (9) ◽  
pp. 2080-2087
Author(s):  
Michael J. Zacuto ◽  
Joseph Perona ◽  
Robert Dunn

1981 ◽  
Vol 34 (3) ◽  
pp. 583 ◽  
Author(s):  
JA Elix ◽  
L Lajide

Connorstictic acid (2) was isolated from the lichen Lecidea aspidula as the corresponding tetraacetate(3). The structure of the latter compound was confirmed by synthesis in several steps from the known depsidone, norstictic acid (4). Direct reduction of norstictic acid with sodium triacetoxyborohydride led to the formation of connorstictic acid.


Author(s):  
DENNIS H. BURNS ◽  
MICHAEL W. BURDEN ◽  
YUE HU LI

A method for the preparation of an α-formylated pyrrole or dipyrromethane which contains an electron-withdrawing β-acetyl is described. Formylation proceeds directly from the corresponding acid pyrrole or dipyrromethane without the need of the usual two-step acid decarboxylation/formylation procedure. The acid is first transformed into its acid chloride with oxalyl chloride, followed by reduction to the aldehyde with the mild reducing agent sodium triacetoxyborohydride, in a one-pot reaction. The non-basic acylating reagent PR 3 is necessary both for acyl chloride formation and for the reduction to succeed.


Synlett ◽  
2010 ◽  
Vol 2010 (11) ◽  
pp. 1729-1730
Author(s):  
Lakhinath Saikia

1990 ◽  
Vol 31 (39) ◽  
pp. 5595-5598 ◽  
Author(s):  
Ahmed F. Abdel-Magid ◽  
Cynthia A. Maryanoff ◽  
Kenneth G. Carson

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