An Expedient and Short Synthesis of a 6-Iodo Isocoumarin Building Block for the Rubromycin Family and its First Palladium-Catalyzed Couplings

Synlett ◽  
2004 ◽  
Vol 2004 (15) ◽  
pp. 2736-2738 ◽  
Author(s):  
Hans-Ulrich Reissig ◽  
Malte Brasholz
Keyword(s):  
Building Block ◽  
Palladium Catalyzed ◽  
Short Synthesis

1‐Bromo‐2‐(cyclopropylidenemethyl)benzene: A Useful Building Block in the Palladium‐Catalyzed Reaction of 2‐Alkynylbenzenamine

2012 ◽  
Vol 7 (7) ◽  
pp. 1691-1696 ◽  
Author(s):  
Shaoyu Li ◽  
Yong Luo ◽  
Xiaocong Wang ◽  
Minjie Guo ◽  
Jie Wu
Keyword(s):  
Building Block ◽  
Palladium Catalyzed

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO), a Versatile Precursor for Trifluoromethyl-Substituted Heteroarenes – a Short Synthesis of Celebrex® (Celecoxib)

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 121-125 ◽  
Author(s):  
Andreas Kirschning ◽  
Heiko Sommer ◽  
Max Braun ◽  
Benjamin Schröder
Keyword(s):  
Building Block ◽  
Synthetic Approach ◽  
Elimination Reaction ◽  
Stetter Reaction ◽  
Inflammatory Drug ◽  
Short Synthesis ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Key Steps

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (ETFBO) serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted thiophenes, furans, pyrrols, and piperazines. Key steps are an addition–elimination reaction to ETFBO followed by the thiazolium-catalyzed Stetter reaction. The scope of this chemistry was demonstrated in a new synthetic approach towards the COX-2 selective, nonsteroidal anti-inflammatory drug Celebrex® (celecoxib).

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