Literature DB >> 16986958

Synthesis of a ketone analogue of biotin via the intramolecular Pauson-Khand reaction.

Eric McNeill1, Irwin Chen, Alice Y Ting.   

Abstract

We report an improved synthesis of 5-(5-oxohexahydrocyclopenta[c]thiophen-1-yl)pentanoic acid (ketone biotin, 1) based on the intramolecular Pauson-Khand cyclization. The synthesis proceeds in eight steps and in 2.7% overall yield from cyclohexene.

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Year:  2006        PMID： 16986958      PMCID： PMC2531226          DOI： 10.1021/ol061862t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes.

Authors:  N K Anand; E M Carreira
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

Review 2.  Site-specific labeling of proteins with small molecules in live cells.

Authors:  Irwin Chen; Alice Y Ting
Journal:  Curr Opin Biotechnol       Date:  2005-02       Impact factor: 9.740

3.  Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase.

Authors:  Irwin Chen; Mark Howarth; Weiying Lin; Alice Y Ting
Journal:  Nat Methods       Date:  2005-01-21       Impact factor: 28.547
  3 in total
  2 in total

1.  Rapid Synthesis of the epi-Biotin Sulfone via Tandem S,N-Carbonyl Migration/aza-Michael/Spirocyclization and Haller-Bauer Reaction.

Authors:  Subhash P Chavan; Dinesh B Kalbhor; Rajesh G Gonnade
Journal:  ACS Omega       Date:  2022-05-12

2.  Phage display evolution of a peptide substrate for yeast biotin ligase and application to two-color quantum dot labeling of cell surface proteins.

Authors:  Irwin Chen; Yoon-Aa Choi; Alice Y Ting
Journal:  J Am Chem Soc       Date:  2007-05-02       Impact factor: 15.419
  2 in total

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